- A Bispidol Chelator with a Phosphonate Pendant Arm: Synthesis, Cu(II) Complexation, and 64Cu Labeling
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Here we present the synthesis and characterization of a new bispidine (3,7-diazabicyclo[3.3.1]nonane) ligand with N-methanephosphonate substituents (L2). Its physicochemical properties in water, as well as those of the corresponding Cu(II) and Zn(II) complexes, have been evaluated by using UV-visible absorption spectroscopy, potentiometry, 1H and 31P NMR, and cyclic voltammetry. Radiolabeling experiments with 64CuII have been carried out, showing excellent radiolabeling properties. Quantitative complexation was achieved within 60 min under stoichiometric conditions, at room temperature and in the nanomolar concentration range. It was also demonstrated that the complexation occurred below pH 2. Properties have been compared to those of the analogue bispidol bearing a N-methanecarboxylate substituent (L1). Although both systems meet the required criteria to be used as new chelator for 64/67Cu in terms of the kinetics of formation, thermodynamic stability, selectivity for Cu(II), and kinetic inertness regarding redox- or acid-assisted decomplexation processes, substitution of the carboxylic acid function by the phosphonic moiety is responsible for a significant increase in the thermodynamic stability of the Cu(II) complex (+2 log units for pCu) and also leads to an increase in the radiochemical yields with 64CuII which is quantitative for L2.
- Gillet, Rapha?l,Roux, Amandine,Brandel, Jérémy,Huclier-Markai, Sandrine,Camerel, Franck,Jeannin, Olivier,Nonat, Aline M.,Charbonnière, Lo?c J.
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- 1-(N-Acylamino)alkylphosphonic acids—Deacylation in aqueous solutions
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The 1-(N-acylamino)alkylphosphonic acids (AC)-AAP belong to the interesting and potentially of pharmacological importance group of 1-aminoalkylphosphonic acids derivatives. Since susceptibility of (AC)-AAP on hydrolytic deacylation can form important factor influencing their biological activity, we have undertaken deacylation investigations of these compounds in aqueous media. In this article, we present our results on deacylation of various types of 1-(N-acylamino)alkylphosphonic acids (AC)-AAP, including 1-(N-acetylamino)alkyl-phosphonic Ac-AAP, 1-(N-chloroacetylamino)alkylphosphonic acids Mca-AAP, 1-(N-trifluoroacetylamino)alkylphosphonic acids TFA-AAP, and 1-(N-benzoylamino)-alkylphosphonic Bz-AAP, derived from representative 1-aminoalkylphosphonic acids AAP (GlyP, AlaP, ValP, PglP, and PheP) in neutral and 2?M HCl solutions.
- Cypryk, Marek,Drabowicz, Jozef,Gostynski, Bartlomiej,Kudzin, Marcin H.,Kudzin, Zbigniew H.,Urbaniak, Pawel
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- 1-(Acylamino)alkylphosphonic acids—alkaline deacylation
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The alkaline deacylation of a representative series of 1-(acylamino)alkylphosphonic acids [(AC)-AAP: (AC) = Ac, TFA, Bz; AAP = GlyP, AlaP, ValP, PglP and PheP] in an aqueous solution of KOH (2M) was investigated. The results suggested a two-stage reaction mechanism with a quick interaction of the hydroxyl ion on the carbonyl function of the amide R-C(O)-N(H)- group in the first stage, which leads to instant formation of the intermediary acyl-hydroxyl adducts of R-C(O?)2-N(H)-, visible in the 31P NMR spectra. In the second stage, these intermediates decompose slowly by splitting of the RC(O?)2-N(H)- function with the subsequent formation of 1-aminoalkylphosphonate and carboxylate ions.
- Cypryk, Marek,Drabowicz, Jozef,Gostynski, Bartlomiej,Kudzin, Marcin H.,Kudzin, Zbigniew H,Urbaniak, Pawel
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- Effect of the nature of carbon catalysts on glyphosate synthesis
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Aqueous solutions of PMIDA (N-phosphonomethyliminodiacetic acid) were oxidized, using air, to obtain glyphosate (N-(phosphonomethyl)glycine) an active herbicide. The oxidative decarboxylation reaction was catalyzed selectively by active carbons obtained from different precursors and modified by specific thermal treatments. The activities were highly dependent upon the functional groups present on the carbon surface. Nitrogen-containing functional groups greatly enhanced the oxidation rates; these groups were either issued from the carbon precursors or introduced by thermal treatment under NH3 of active carbons. The highest rates of PMIDA oxidation were obtained using nonactivated carbons treated with NH3 at 900°C. Activities were also enhanced by thermal treatments at 900°C under N2 which eliminated the acidic sites from the carbon surface, and possibly created active basic sites.
- Pinel, Catherine,Landrivon, Emmanuel,Lini, Hedi,Gallezot, Pierre
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- Comments on the Synthesis of Aminomethylphosphonic Acid
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Two simple methods for the synthesis of aminomethylphosphonic acid from phosphorus(III) chloride and 1,3,5-triacylhexahydro-1,3,5-triazine or N-(hydroxymethyl)benzamide are described.
- Soroka, Miroslaw
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- Homogeneous catalysts for selective molecular oxygen driven oxidative decarboxylations
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Cobalt(II) ion has been found to catalyze the molecular oxygen driven oxidation of N-(phosphonomethyl)iminodiacetic acid (PMIDA) to N-(phosphonomethyl)glycine (PMG) in aqueous solution.1 This homogeneous catalytic conversion is novel and represents, in effect, an oxidative dealkylation of one carboxymethyl moiety yielding the N-substituted glycine. The reaction is selective to the desired product PMG when carried out at the natural pH of the free acid substrate (~ 1-2) and when carried out at substrate loadings less than 5% by weight. In addition, the catalytic system is selective for the PMIDA substrate; i.e., other closely related ligands show no reactivity, e.g., NTA, EDTA, etc. The results of kinetic and mechanistic studies on dilute systems are presented and discussed with special emphasis on how an understanding of the mechanism can make it possible to generate a catalyst system that gives high yields even with high substrate loadings. The reactions are first-order in substrate and [Co]t. The oxygen pressure dependence exhibits saturation kinetics, while the selectivity increases as oxygen pressure increases. The rate is also inversely proportional to [H+]. The high selectivity of the oxidation and the unique selectivity of the cobalt catalytic system for the PMIDA substrate are discussed in terms of the magnitude of the metal ligand binding constant at the low pH of the reaction.
- Riley, Dennis P.,Fields, Donald L.,Rivers, Willie
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- Chemical and Mutagenic Analysis of Aminomethylphosphonate Biodegradation
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Utilization of aminomethyl-, N-methylaminomethyl-, N,N-dimethylaminomethyl-, and N-acetylaminomethylphosphonate by Escherichia coli as a sole source of phosphorus during growth resulted in the extracellular generation of N-methylacetamide, N,N-dimethylacetamide, trimethylamine, and N-methylacetamide, respectively.Product identification relied on synthesis of (13)C-enriched aminomethylphosphonates followed by (1)H NMR analysis of products isolated from the biodegradation of the labeled and unlabeled phosphorus sources.To circumvent the requirement of an intact cell for carbon to phosphorus bond degradation, transposon mutagenesis was exploited as a complement to the chemical analysis.E. coli K-12 were infected with λTn5.Colonies resistant to kanamycin were selected and then screened for loss of the ability to use ethylphosphonate as a sole source of phosphorus.The mutant identified, E. coli SL724, was also unable to degrade aminomethylphosphonates.This combination of chemical and mutagenic analysis points toward a shared mechanism between alkyl- and aminomethylphosphonate biodegradation.
- Avila, L. Z.,Loo, S. H.,Frost, J. W.
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- PROCESS FOR OXIDATION OF N-(PHOSPHONOMETHYL)IMINODIACETIC ACID
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An oxidation catalyst is prepared by pyrolyzing a source of iron and a source of nitrogen on a carbon support. Preferably, a noble metal is deposited over the modified support which comprises iron and nitrogen bound to the carbon support. The catalyst is effective for oxidation reactions such as the oxidative cleavage of tertiary amines to produce secondary amines, especially the oxidation of N-(phosphonomethyl)iminodiacetic acid to N-(phosphonomethyl)-glycine.
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Paragraph 0104
(2015/11/10)
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- METHOD FOR THE SYNTHESIS OF AMINOALKYLENEPHOSPHONIC ACID
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The present invention is related to a method for the synthesis of an aminoalkylenephosphonic acid or its phosphonate esters comprising the following steps: a) forming, in the presence of an aldehyde or ketone and an acid catalyst, a reaction mixture by mixing a compound comprising at least one HNR1R2 moiety or a salt thereof, with a compound having one or more P-O-P anhydride moieties, said moieties comprising one P atom at the oxidation state (+III) and one P atom at the oxidation state (+III) or (+V), wherein the ratio of moles of aldehyde or ketone to N-H moieties is 1 or more and wherein the ratio of N-H moieties to P-O-P anhydride moieties is 0.3 or more and, b) recovering the resulting aminoalkylenephosphonic acid comprising compound or its phosphonate esters.
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Paragraph 0073
(2014/02/15)
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- METHOD FOR THE SYNTHESIS OF ALPHA-AMINOALKYLENEPHOSPHONIC ACID
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The present invention is related to a new method for the synthesis of alpha-aminoalkylenephosphonic acid or its phosphonate esters comprising the steps of forming a reaction mixture by mixing a P-O-P anhydride moiety comprising compound, having one P-atom at the oxidation state (+111) and the other P-atom at the oxidation state (+111) or (+V), an aminoalkanecarboxylic acid and an acid catalyst, wherein said reaction mixture comprises an equivalent ratio of alpha-aminoalkylene carboxylic acid to P-O-P anhydride moieties of at least 0.2, and recovering the resulting alpha-aminoalkylene phosphonic acid compound or an ester thereof from the reaction mixture.
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Page/Page column 23
(2014/02/15)
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- Tritylamine (triphenylmethylamine) in organic synthesis; III. The synthesis of 1-aminoalkylphosphonic acids in the reaction of N-(triphenylmethyl) alkanimines with phosphorus trichloride in acetic acid or with phosphonic (phosphorous) acid in acetic anhydride
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The reaction of phosphorus trichloride in acetic acid or phosphonic (phosphorous) acid in acetic anhydride, with N-(triphenylmethyl)alkanimines gives 1-acetylaminoalkylphosphonic acids 1a-j, which after hydrolysis give 1-aminoalkylphosphonic acids 2a-j in good yields. ARKAT USA, Inc.
- Goldeman, Waldemar,Soroka, Miroslaw
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experimental part
p. 360 - 369
(2011/02/27)
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- A mild and convenient oxidation of H-phosphinic acids
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A new mild and convenient method of oxidation of H-phosphinic to the corresponding phosphonic acids was developed. Conversion of H-phosphinic acids into trivalent trimethylsilyl esters using hexamethyldisilazane, followed by their oxidation with air and subsequent methanolysis allowed obtaining the final compounds in good to excellent yields. The methodology was proved to be particularly useful for N-benzyloxycarbonyl-α-aminophosphinic acids. The scope and limitations of the reaction were additionally tested using a variety of both free and protected amino- and hydroxyphosphinates as substrates.
- Berlicki,Mucha,Kafarski
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p. 1959 - 1962
(2008/09/19)
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- Method and compositions for identifying anti-HIV therapeutic compounds
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Methods are provided for identifying anti-HIV therapeutic compounds substituted with carboxyl ester or phosphonate ester groups. Libraries of such compounds are screened optionally using the novel enzyme GS-7340 Ester Hydrolase. Compositions and methods relating to GS-7340 Ester Hydrolase also are provided.
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- Process for the preparation of N-phosphonomethylglycine and derivatives thereof
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N-phosphonomethylamines are produced by reaction of an amine substrate with a halomethylphosphonic acid or salt thereof, a hydroxymethylphosphonic acid or salt thereof, or a dehydrated self-ester dimer, trimer or oligomer of hydroxymethylphosphonic acid. Among the products that may be prepared according to the process are N-phosphonomethylaminocarboxylic acids such as (e.g.) glyphosate, N-phosphonomethylaminoalkanols such as (e.g.) hydroxyethlaminomethylphosphonic acid, and N-acylaminomethylphosphonic acids such as (e.g.) N-carbamylaminomethylphosphonic acid. Certain reactions are conducted with a substantial excess of amine reactant in order to drive the conversion while avoiding excessive formation of bis(N-phosphonomethyl)amine by-products. Other reactions use a secondary amine substrate (such as iminodiacetic acid) and can be conducted at substantial equimolar ratios of halomethylaminomethylphosphonic acid or hydroxyaminomethylphosphonic acid to secondary amine reactant without significant formation of bis(phosphonomethyl)amine by-products. Further disclosed is a process for the preparation of hydroxymethylphosphonic acid self-ester dimers, trimers and oligomers by azeotropic dehydration.
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Page/Page column 34
(2010/02/11)
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- Method and compositions for identifying anti-HIV therapeutic compounds
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Methods are provided for identifying anti-HIV therapeutic compounds substituted with carboxyl ester or phosphonate ester groups. Libraries of such compounds are screened optionally using the novel enzyme GS-7340 Ester Hydrolase. Compositions and methods relating to GS-7340 Ester Hydrolase also are provided.
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- CONTINUOUS PROCESS FOR PREPARING N-PHOSPHONOMETHYL GLYCINE
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In general the present invention relates to a continuous process for manufacturing (N-phosphonomethyl) glycine, glyphosate, by the catalyzed oxidation of N-phosphono-methyliminodiacetic acid. Glyphosate can be provided in high yield and in a cost efficient process by minimizing the competing side reactions and by-products. The process includes conducting the oxidation reaction and selecting an appropriate catalyst to maximize the rate of the oxidation of N-phosphonomethyliminodiacetic acid while at the same time minimizing the rate of oxidation of glyphosate in the same reaction.
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- Method for preparing aminomethylphosphonate derivatives via hydrogenation of cyanophosphonate derivatives
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A novel process for preparing aminomethylphosphonate derivatives involves the hydrogenation of cyanophosphonate derivatives in the presence of a catalyst to produce aminomethylphosphonate derivatives.
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- Process for the preparation of aminomethanephosphonic acid and aminomethylphosphinic acids
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Aminomethanephosphonic acid and aminomethylphosphinic acids are interesting as biologically active compounds or as intermediates for the preparation of biologically active compounds. According to the invention, such compounds of the formula I STR1 in which R1 is OH, C1 -C4 -alkyl or phenyl, can be prepared in a technically simple manner by reacting compounds of the formula II STR2 in which R2 is H, C1 -C6 -alkyl, benzyl, phenyl, optionally substituted by C1 -C4 -alkyl, -alkoxy and/or halogen, and R1 is as defined above, with water, at 80° to 300° C.
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- Process for the manufacture of aminomethanephosphonic acid
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A process for the manufacture of aminomethanephosphonic acid comprises: a) reacting a compound of formula R--CH2 --NH--CO--NH--CH2 --R' wherein R and R', which may be the same or different, represent a phosphonation leaving group with a phosphonating agent and subsequently b) hydrolysing the product of step (a) to form aminomethanephosphonic acid.
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- PREPARATION DE L'ACIDE AMINOMETHYLPHOSPHONIQUE α-DIDEUTERIE
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Nucleophilic amination of chloromethylphosphonic esters was studied, α-Dideuteriated aminomethylphosphonic acid was obtained from bis(trifluoroethyl) chloromethylphosphonic ester and sodium azide through substitution of the chlorine, reduction of the azide and acidic hydrolysis.Incorporation of the deuterium was greated than 95percent and overall yields were in the range 55-65percent. Key words: nucleophili amination, chloromethylphosphonic esters, α-dideuteriated chloromethylphosphonic esters, sodium azide, aminomethylphosphonic acid, deuterium oxide, trifluoroethanol d, α-dideuteriated aminomethylphosphonic acid.
- Berte-Verrando, Sylvie,Nief, Francois,Patois, Carl,Savignac, Philippe
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- ORGANOPHOSPHORUS COMPOUNDS AS POTENTIAL FUNGICIDES. PART II. AMINOALKANE-, GUANIDINOALKANE-, AND THIOUREIDOALKANE-PHOSPHONIC ACIDS: PREPARATION, SPECTROSCOPY, AND FUNGICIDAL ACTIVITY
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A range of α-amino-, ω-amino-, α-guanidino-, and ω-guanidinoalkanephosphonic acids has been prepared for the purpose of studying their spectroscopic features and fungicidal activity.In addition, α-thioureido-octanephosphonic acid and thioureylene-1,1-bis(1-octanephosphonic acid) were isolated during the preparation of α-guanidino-octanephosphonic acid. 31P, 1H, and 13C nmr spectral data which were obtained for solutions of the amino- and guanidino-compounds in D2O or D2O/D2SO4, and for the thioureido compounds in DMSO-d6, are discussed together with previouslyreported data for the aminophosphonic types.FAB mass spectrometry generally gives strong pseudomolecular ions + for the zwitterionic amino- and guanidino-compounds with relatively simple fragmentations.Fungicidal activity of the α-aminophosphonic acids was found to be greater than for the ω-amino compounds, with maximum activity at a chain length of three carbon atoms when used as a seed dressing for the control of Drechslera spp.Moderately good activity was shown by the thioureido compounds against a number of fungal organisms in vitro but the guanidino-compounds exhibited low activity.Key words: Organophosphorus; fungicides; aminophosphonic acids; guanidinophosphonic acids; NMR spectroscopy; FAB mass spectroscopy.
- Cameron, David G.,Hudson, Harry R.,Pianka, Max
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- Preparation of N-acyl-aminomethylphosphonates
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N-Acyl-aminomethylphosphonic acids represented by the formula STR1 wherein R is selected from the group consisting of methyl and aryl are prepared by: (a) bringing together under substantially anhydrous reaction conditions an amide represented by the formula STR2 wherein R is as defined above and paraformaldehyde; and thereafter, (b) adding phosphorous trihalide to the reaction mixture.
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- The Synthesis of 1-Aminoalkylphosphonic Acids. A Revised Mechanism of the Reaction of Phosphorus Trichloride, Amides and Aldehydes or Ketones in Acetic Acid (Oleksyszyn Reaction)
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The mechanism of the amidoalkylation of trivalent phosphorus compounds in acetic acid has been reinvestigated.Evidence is presented that 1-(acylamino)alkyl acetates 5 and not N,N'-alkylidenebisamides 2 are the intermediates in this reaction.Supporting literature analogies are discussed.This paper also describes a convenient procedure for the preparation of crude (acylamino)alkyl alkanoates 5, which are excellent amidoalkylating agents.The usefulness of these reagents is demonstrated by a simple two-step "one pot" synthesis of 1-aminoalkylphosphinic acids 1.
- Soroka, Miroslaw
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p. 331 - 334
(2007/10/02)
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- Oxidation/dealkylation process
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There is disclosed a process for producing the alkali metal salts of N-phosphonomethylglycine which comprises heating to an elevated temperature a di-alkali metal salt of N-alkyl-N-(2-hydroxyethyl)aminomethylphosphonic acid.
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- Process for the preparation of α-aminoalkylphosphonic acids
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A process for the production of α-aminoalkylphosphonic acids or salts thereof of the formula A STR1 wherein R1 represents hydrogen, alkyl having from 1 to 4 carbon atoms or CH2 --C6 H5 and X hydrogen or a metal cation, which comprises reacting a compound of the formula B STR2 in which R1 has the same meaning as in formula A and Mp≈ represents hydrogen or a p-valent metal cation, with a hypohalite of a p-valent metal cation, and isolating the metal salt produced or acidifying the reaction mixture obtained to produce the α-aminoalkyl-phosphonic acid.
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- Process for the preparation of α-aminoalkylphosphonic acids and of α-aminoalkylphosphinic acids
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α-Aminoalkylphosphonic and α-aminoalkylphosphinic acids of the formula I STR1 where n=1 or 0, R1 =H, CH3 or CH2 --C6 H5 R2 =H (for n=1) and also=alkyl or phenyl (for n=0) are prepared by Hofmann deradation from compounds of the formula II STR2 wherein n and R1 have the same meaning as in formula I, R3 =alkyl (for n=1), alkyl or phenyl (for n=0), and Mp+ =p-valent cation, with subsequent working up in the known manner. Some of the compounds I are biologically active, and some are intermediates for the preparation of biologically active compounds.
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- ORGANIC PHOSPHORUS COMPOUNDS 89. A NEW METHOD FOR THE PREPARATION OF AMINOMETHYLPHOSPHONIC ACID AND DERIVATIVES
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A high yield preparation of aminomethylphosphonic acid and derivatives, 1, 2 and 3, involves heating of N,N',N''-tris(alkoxycarbonyl)hexahydrotriazines with sec. phosphites in the presence of BF3*Et2O as a catalyst followed by hydrolysis.Without catalyst no reaction occurs.This reaction has also been used to obtain O-ethyl N-ethoxyarbonylaminomethyl-methylphosphinate, 4.Interaction of 1 and ethylbromoacetate in the presence of NaH, followed by hydrolysis produces glyphosphate 5 in high yield.
- Maier, Ludwig
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p. 361 - 365
(2007/10/02)
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- Synthesis of 1-Aminoalkylphosphonic Acids via Amidoalkylation of Phosphorous Acid by N,N'-Alkylidenbisamides
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N,N'-Alkylidenebisamides 1, totally unsuitable as amidoalkylating agents toward phosphorous acid, react with its "activated" form prepared "in situ" from phosphorous(III) chloride and acetic acid to give the desired 1-amidoalkylphosphonic acids 2 in high yield.
- Soroka, Miroslaw,Jaworska, Dorota,Szczesny, Zbigniew
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p. 1153 - 1155
(2007/10/02)
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- Synthesis, Enzyme-Substrate Interaction, and Herbicidal Activity of Phosphoryl Analogues of Glycine
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The interactions of hydrophosphoryl compounds 1-10 and 1,3,5-triacetylhexahydro-1,3,5-triazine furnish the N-acetylated (aminomethyl)phosphoryl compounds 11-20, which, upon acidic hydrolysis, lead to 3, 6, 9, and 21-24.Strict selectivity is observed in the enzyme-catalyzed hydrolysis with the enzymes α-chymotrypsin, phosphodiesterase I, and alkaline phosphatase.Some of the synthesized materials exhibit herbicidal and antitumor activity.
- Natchev, Ivan A.
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p. 861 - 868
(2007/10/02)
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- (Phosphonomethyl)trifluoromethyl sulfonates
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The compound (phosphonomethyl)perfluoroalkyl sulfonate can be represented by the formula STR1 wherein n is from 0 to 7 and R and R1 are independently selected from the group consisting of hydrogen, 2-cyanoethyl, monovalent hydrocarbons containing from 1 to 18 carbons, monovalent hydrocarbonoxyhydrocarbons containing from 1 to 18 carbons, halogenated monovalent hydrocarbons containing from 1 to 18 carbons and from 1 to 3 halogens, halogenated monovalent hydrocarbonoxyhydrocarbons containing from 1 to 18 carbons and from 1 to 3 halogens. The compound is useful as an intermediate to prepare amino-phosphorous compounds such as N-phosphonomethylglycine.
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- CONVERSION OF AMINO ACIDS AND DIPEPTIDES INTO THEIR PHOSPHONIC ANALOGS; Aminoalkylphosphonic acids and peptides II.
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Acylamino carboxylic acids were degradated by the Hunsdiecker-reaction; the bromo-derivatives were reacted with NaPO(OC2H5)2.Aminophosphonic acids were obtained by acidic hydrolysis, and half-blocked derivatives by the selective removal of masking substituents.Two phosphonopeptides were also prepared by this route.
- Oesapay, George,Szilagyi, Ildiko,Seres, Jenoe
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p. 2977 - 2984
(2007/10/02)
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- A CONVENIENT SYNTHESIS OF AMINOMETHYLPHOSPHONIC ACID
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A novel procedure for the preparation of aminomethylphosphonic acid (AMPA) is described.This compound, which has been shown to have some biological activity, is synthesized by treating N-hydroxymethylbenzamide with a mixture of phosphorous trichloride and trimethyl phosphite, followed by hydrolysis of the ester intermediate.
- Pulwer, Mitchell J.,Balthazor, Terry M.
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p. 733 - 740
(2007/10/02)
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- SYNTHESIS AND REACTIVITY OF DIETHYL PHOSPHONOMETHYLTRIFLATE
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Diethyl phosphonomethyltriflate, prepared from diethyl hydroxymethylphosphonate, readily reacts in good to excellent yields with a variety of oxygen and nitrogen nucleophiles.
- Phillion, Dennis P.,Andrew, Steven S.
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p. 1477 - 1480
(2007/10/02)
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- Oxidative ring cleavage process
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The novel reaction of 4-morpholinylmethylphosphonic acid with an aqueous alkali yields the trialkali metal salt of N-phosphonomethylglycine.
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- Process for producing aminomethylphosphonic acid
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Aminomethylphosphonic acid is produced by reaction of a hexahydro-1,3,5-triazine-N,N',N -tris-carboxylic acid ester of the formula STR1 wherein R is an alkyl group having 1 to 4 carbon atoms or a phenyl group, in the presence of a Lewis acid as catalyst, with an ester of the phosphorous acid of the formula STR2 wherein R1 is an alkyl group having 1 to 5 carbon atoms, a phenyl group, a benzyl group, the 2-cyanoethyl group or the 2,2,2-trichloroethyl group, to give an N-carboxyaminomethylphosphonic acid derivative of the formula STR3 and subsequent hydrolysis thereof in an aqueous medium and in the presence of a strong acid. Aminomethylphosphonic acid can be used as active substance for influencing plant growth, and as intermediate for producing herbicidal active substances.
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- Synthesis of 1-Aminoalkane Phosphonic Acids via Benzhydrylic Schiff Bases
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A simple synthesis of 1-aminoalkanephosphonic acids is described.The addition of diethylphosphite to alkylidene- and arylidenebenzhydrylamines yields the N-benzhydryl-1-aminoalkanephosphonic acid esters.The title compounds are formed by treatment of the N-blocked esters with hydrobromic acid.The starting amine can be recycled from the hydrylbromide. - Key words: 1-Aminoalkane Phosphonic Acids, Benzhydrylic, Schiff Bases
- Issleib, Kurt,Doepfer, Klaus-Peter,Balszuweit, Arno
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p. 1392 - 1394
(2007/10/02)
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- Piperazine phosphonic acids
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Nitrogen-heterocyclic phosphonic acids and derivatives thereof characterized by aminomethyl (or substituted methyl) phosphonic acids or derivatives thereof bonded directly or indirectly, i.e., through a N-side chain to the nitrogen atom in the heterocyclic ring, for example those containing in the molecule at least one of the following units: EQU1 where N represents a heterocyclic ring having a nitrogen atom on the ring; --R'N-- represents an amino-terminated side chain attached directly to the ring nitrogen (which side chain may or may not be present); and EQU2 represents a methyl (or substituted methyl) phosphonic acid group where M is hydrogen, an alcohol or a salt moiety, and X and Y are hydrogen or a substituted group such as alkyl, aryl, etc., of which one or two units may be present depending on the available nitrogen bonded hydrogens, and to uses for these compounds, for example, as scale inhibitors, corrosion inhibitors, etc.
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