672-87-7

Basic information

• Product Name: ALPHA-METHYL-L-P-TYROSINE
• Synonyms: (S)-2-AMINO-2-METHYL-3-(4'-HYDROXYPHENYL)PROPANOIC ACID;AMPT;ALPHA-METHYLTYROSINE;ALPHA-METHYL-L-P-TYROSINE;ALPHA-METHYL-L-TYR;ALPHA-METHYL-L-TYROSINE;A-METHYL-L-P-TYROSINE;H-(ME)TYR-OH
• CAS NO: 672-87-7
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.22
• EINECS: 211-599-5
• Product Categories: Amino acids methyl、ethyl、t-butyl series;Amino Acids & Derivatives;Aromatics;Chiral Reagents;α-Methyl Amino Acids
• Mol File: 672-87-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 320-340°C dec.
• Boiling Point: 383.7oC at 760 mmHg
• Flash Point: 185.9oC
• Appearance: White to pale yellow/Powder
• Density: 1.283g/cm3
• Vapor Pressure: 1.42E-06mmHg at 25°C
• Refractive Index: 1.599
• Storage Temp.: −20°C
• Solubility: Aqueous Acid (Slightly)
• PKA: pKa 2.7 (Uncertain);10.1 (Uncertain)
• Merck: 13,6183
• BRN: 2368400
• CAS DataBase Reference: ALPHA-METHYL-L-P-TYROSINE(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA-METHYL-L-P-TYROSINE(672-87-7)
• EPA Substance Registry System: ALPHA-METHYL-L-P-TYROSINE(672-87-7)

Safety Data

• Statements: 22-38-40-48/20/22
• Safety Statements: 22-24/25
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 672-87-7(Hazardous Substances Data)

Usage

Description

ALPHA-METHYL-L-P-TYROSINE, also known as α-Methyl-L-tyrosine, is an organic compound that serves as a competitive inhibitor of the enzyme tyrosine hydroxylase. It is structurally similar to the amino acid L-tyrosine, with a methyl group added to the alpha carbon. ALPHA-METHYL-L-P-TYROSINE plays a significant role in various applications across different industries due to its ability to modulate the activity of tyrosine hydroxylase.
Used in Pharmaceutical Industry:
ALPHA-METHYL-L-P-TYROSINE is used as an antihypertensive agent for the treatment of pheochromocytoma, a rare tumor of the adrenal gland that can lead to high blood pressure. It functions by inhibiting the enzyme tyrosine hydroxylase, which is crucial for the synthesis of catecholamines, including dopamine, norepinephrine, and epinephrine. By reducing the production of these hormones, ALPHA-METHYL-L-P-TYROSINE helps control blood pressure in patients with pheochromocytoma.
Used in Neuroscientific Research:
ALPHA-METHYL-L-P-TYROSINE is used as a research tool to investigate the role of dopamine and iron-mediated oxidative stress in cell death induced by Fe2+ or methamphetamine (METH). By inhibiting tyrosine hydroxylase, this compound can help determine the dependence of cell death on cytosolic dopamine levels, providing valuable insights into the underlying mechanisms of neurodegeneration and potential therapeutic targets for related conditions.

Originator

Demser,MSD,US,1979

Manufacturing Process

50 g of α-methyl-N-dichloroacetyl-p-nitrophenylalanine was dissolved in 500 ml methanol, 300 mg of platinum oxide were added and the mixture reduced at 41 pounds of pressure; within an hour 14.5 pounds were used up (theory 12.4 pounds). After filtration of the catalyst, the red clear filtrate was concentrated in vacuo and the residual syrup flushed several times with ether. The crystalline residue thus obtained, after air drying, weighed 45.3 g (99.5%), MP unsharp at about 104°C to 108°C with decomposition. After two precipitations with ether from an alcoholic solution, the somewhat hygroscopic amine was dried over sulfuric acid for analysis.10 g of the amine prepared above was dissolved in 5 ml of 50% sulfuric acid at room temperature; the viscous solution was then cooled in ice and a solution of sodium nitrite (2.4 g) in 10 ml water gradually added with agitation. A flocculent precipitate formed. After all the nitrite had been added, the mixture was aged in ice for an hour, after which it was allowed to warm up to room temperature. Nitrogen came off and the precipitate changed to a sticky oil. After heating on the steam bath until evolution of nitrogen ceased, the oil was extracted with ethyl acetate. After removal of the solvent in vacuo, 9.4 g of colored solid residue was obtained, which was refluxed with 150 ml hydrochloric acid (1:1) for 17 hours. The resulting dark solution; after Norite treatment and extraction with ethyl acetate, was concentrated in vacuo to dryness and the tan colored residue (7.4 g) sweetened with ethanol. Dissolution of the residue in minimum amount of ethanol and neutralization with diethylamine of the clarified solution, precipitated the α-methyl tyrosine, which was filtered, washed with ethanol (until free of chlorides) and ether. The crude amino acid melted at 309°C with decomposition. For further purification, it was dissolved in 250 ml of a saturated sulfur dioxide-water solution, and the solution, after Noriting, concentrated to about 80 ml, the tan colored solid filtered washed with ethanol and ether. Obtained 1.5 g of α-methyl tyrosine, MP 320°C dec.

Therapeutic Function

Tyrosine hydroxylase inhibitor

Biochem/physiol Actions

α-Methyl-L-tyrosine (L-AMPT) acts as a competitive inhibitor of tyrosine hydroxylase and inhibits the conversion of tyrosine to L-DOPA and eventually lowers dopamine synthesis in cytosol. AMPT at low concentrations can be used as a potent therapeutic for refractory dystonia or dyskinesia. It also helps in decreasing catecholamine concentration in pheochromocytoma patients.

InChI:InChI=1/C10H13NO3/c1-10(11,9(13)14)6-7-2-4-8(12)5-3-7/h2-5,12H,6,11H2,1H3,(H,13,14)/t10-/m0/s1

Synthetic route

(2S)-2-amino-3-(4-methoxyphenyl)-2-methyl-propionamide hydrogen bromide salt (1299492-19-5) → L-methyltyrosine (672-87-7)

Conditions	Yield
With water; hydrogen bromide at 105℃; for 17h; Product distribution / selectivity;	86%

2-(S)-amino-3-(4-methoxyphenyl)-2-methylpropionamide (1299492-09-3) → L-methyltyrosine (672-87-7)

Conditions	Yield
With water; hydrogen bromide at 120℃; for 5h; Product distribution / selectivity;	84%
Multi-step reaction with 2 steps 1: water; hydrogen bromide / methanol / 100 °C / 15 - 22.5 Torr 2: water; hydrogen bromide / 17 h / 105 °C View Scheme

(2S)-2-amino-3-(4-methoxyphenyl)-2-methyl-propionamide hydrochloride (1299492-14-0) → L-methyltyrosine (672-87-7)

Conditions	Yield
With hydrogen bromide In water at 120℃; for 4h; Product distribution / selectivity;	83%

(2S)-2-amino-3-(4-methoxyphenyl)-2-methylpropionamide formic acid salt (1299492-20-8) → L-methyltyrosine (672-87-7)

Conditions	Yield
With water; hydrogen bromide at 105℃; for 17h; Product distribution / selectivity;	82%

(S)-N2-benzoyl-O4',2-dimethyltyrosine → L-methyltyrosine (672-87-7)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 100℃; for 4h;	75.4%

tert-butyl (2R)-2-amino-3-(4-methoxyphenyl)-2-methylpropanoate → L-methyltyrosine (672-87-7)

Conditions	Yield
Stage #1: tert-butyl (2R)-2-amino-3-(4-methoxyphenyl)-2-methylpropanoate With boron tribromide In dichloromethane at 20℃; for 1.5h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water Product distribution / selectivity;	45.4%

N-Chloroacetyl-α-methyltyrosine (121703-96-6) → L-methyltyrosine (672-87-7) + α-methyl-D-tyrosine (672-86-6) + N-Chloroacetyl-D-α-methyltyrosine (121704-37-8) + N-Chloroacetyl-L-α-methyltyrosine (121703-96-6, 121704-37-8)

Conditions	Yield
With potassium hydroxide; porcine kidney acylase I pH 7.5-8.0; Yields of byproduct given;	A 30% B n/a C n/a D n/a
With potassium hydroxide; porcine kidney acylase I pH 7.5-8.0; Yields of byproduct given;	A n/a B 30% C n/a D n/a
With potassium hydroxide; porcine kidney acylase I pH 7.5-8.0; Yield given. Yields of byproduct given;

α-methyl-β-p-methoxyphenyl-alanine (65555-88-6) → L-methyltyrosine (672-87-7)

Conditions	Yield
With hydrogen bromide

N-Chloroacetyl-α-methyltyrosine (121703-96-6) → L-methyltyrosine (672-87-7) + N-Chloroacetyl-D-α-methyltyrosine (121704-37-8)

Conditions	Yield
With potassium hydroxide; potassium phosphate buffer; porcine kidney acylase I at 40℃; relative initial rate of hydrolysis, also with Aspergillus acylase I as a catalyst; with or without CoCl2;

2-Nitro-2-(4-hydroxybenzyl)propionsaeureethylester (16109-65-2) → L-methyltyrosine (672-87-7)

Conditions	Yield
With hydrogen; platinum(IV) oxide; nickel 1.) MeOH, reflux, 1 h, 2.) MeOH, 28 h; Yield given. Multistep reaction;

(4-hydroxyphenyl)methanol (623-05-2) → L-methyltyrosine (672-87-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 56.1 percent / tetrabutylammonium chloride, potassium fluoride dihydrate / toluene / 48 h / Heating 2: 2.) H2 / 1.) Raney-Ni, 2.) PtO2 / 1.) MeOH, reflux, 1 h, 2.) MeOH, 28 h View Scheme

p-Methoxybenzyl bromide (2746-25-0) → L-methyltyrosine (672-87-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: NaH / tetrahydrofuran / 0 - 25 °C 2: α-chymotrypsin / dimethylsulfoxide; H2O / 22 - 25 °C / potassium phosphate ( pH 7.0); with pig liver esterase the reaction rate is higher but the e.e. is lower 3: 1.) acyl azide formation, 2.) Curtius rearrangement 4: aq. HBr (48 percent) View Scheme

2-<(4-methoxyphenyl)methyl>-2-methylpropanedioic acid, dimethyl ester (21118-89-8) → L-methyltyrosine (672-87-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: α-chymotrypsin / dimethylsulfoxide; H2O / 22 - 25 °C / potassium phosphate ( pH 7.0); with pig liver esterase the reaction rate is higher but the e.e. is lower 2: 1.) acyl azide formation, 2.) Curtius rearrangement 3: aq. HBr (48 percent) View Scheme

(R)-2-(4-Methoxy-benzyl)-2-methyl-malonic acid monomethyl ester (21186-54-9) → L-methyltyrosine (672-87-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) acyl azide formation, 2.) Curtius rearrangement 2: aq. HBr (48 percent) View Scheme

4-methoxybenzyl methyl ketone (122-84-9) → L-methyltyrosine (672-87-7)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: water; methanol / 20 h / 40 °C / Sealed tube 2.1: sulfuric acid / dichloromethane; water / 3.25 h / -10 - 0 °C / Cooling with ice 2.2: pH 8 - 9 3.1: ammonium formate / palladium on carbon / isopropyl alcohol / 1 h / Inert atmosphere; Reflux 4.1: water; hydrogen bromide / methanol / 100 °C / 15 - 22.5 Torr 5.1: water; hydrogen bromide / 17 h / 105 °C View Scheme
Multi-step reaction with 4 steps 1.1: water; methanol / 20 h / 40 °C / Sealed tube 2.1: sulfuric acid / dichloromethane; water / 3.25 h / -10 - 0 °C / Cooling with ice 2.2: pH 8 - 9 3.1: palladium on carbon / water; methanol / 5.75 h / 20 - 60 °C 4.1: water; hydrogen bromide / 17 h / 105 °C View Scheme
Multi-step reaction with 4 steps 1.1: water; methanol / 20 h / 40 °C / Sealed tube 2.1: sulfuric acid / dichloromethane; water / 3.25 h / -10 - 0 °C / Cooling with ice 2.2: pH 8 - 9 3.1: ammonium formate / palladium on carbon / isopropyl alcohol / 1 h / Inert atmosphere; Reflux 4.1: water; hydrogen bromide / 5 h / 120 °C View Scheme

2-[1-(S)-cyano-2-(4-methoxyphenyl)-1-methylethylamino]-2-(R)-phenylacetamide (1299492-07-1) → L-methyltyrosine (672-87-7)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sulfuric acid / dichloromethane; water / 3.25 h / -10 - 0 °C / Cooling with ice 1.2: pH 8 - 9 2.1: ammonium formate / palladium on carbon / isopropyl alcohol / 1 h / Inert atmosphere; Reflux 3.1: water; hydrogen bromide / methanol / 100 °C / 15 - 22.5 Torr 4.1: water; hydrogen bromide / 17 h / 105 °C View Scheme
Multi-step reaction with 3 steps 1.1: sulfuric acid / dichloromethane; water / 3.25 h / -10 - 0 °C / Cooling with ice 1.2: pH 8 - 9 2.1: palladium on carbon / water; methanol / 5.75 h / 20 - 60 °C 3.1: water; hydrogen bromide / 17 h / 105 °C View Scheme
Multi-step reaction with 3 steps 1.1: sulfuric acid / dichloromethane; water / 3.25 h / -10 - 0 °C / Cooling with ice 1.2: pH 8 - 9 2.1: ammonium formate / palladium on carbon / isopropyl alcohol / 1 h / Inert atmosphere; Reflux 3.1: water; hydrogen bromide / 5 h / 120 °C View Scheme

2-[(R)-(carbamoylphenylmethyl)-amino]-3-(4-methoxyphenyl)-2-(S)-methylpropionamide (1299492-08-2) → L-methyltyrosine (672-87-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: ammonium formate / palladium on carbon / isopropyl alcohol / 1 h / Inert atmosphere; Reflux 2: water; hydrogen bromide / methanol / 100 °C / 15 - 22.5 Torr 3: water; hydrogen bromide / 17 h / 105 °C View Scheme
Multi-step reaction with 2 steps 1: ammonium formate / palladium on carbon / isopropyl alcohol / 1 h / Inert atmosphere; Reflux 2: water; hydrogen bromide / 5 h / 120 °C View Scheme
Multi-step reaction with 2 steps 1: palladium on carbon / water; methanol / 5.75 h / 20 - 60 °C 2: water; hydrogen bromide / 17 h / 105 °C View Scheme

3-(4-methoxyphenyl)-2-methyl-2-((S)-1-phenyl-ethylamino)-propionamide (1299492-11-7) → L-methyltyrosine (672-87-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride / isopropyl alcohol; water 2: hydrogen / palladium on carbon / methanol / 1.33 h / 50 °C / 2250.23 Torr 3: hydrogen bromide / water / 4 h / 120 °C View Scheme

3-(4-methoxyphenyl)-2-methyl-2-((1S)-1-phenyl-ethylamino)-propionamide hydrochloride (1299492-12-8) → L-methyltyrosine (672-87-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 2-methyl-propan-1-ol / Heating; Reflux 2: hydrogen / palladium on carbon / methanol / 1.33 h / 50 °C / 2250.23 Torr 3: hydrogen bromide / water / 4 h / 120 °C View Scheme

(2S)-3-(4-methoxyphenyl)-2-methyl-2-((1S)-1-phenyl-ethylamino)-propionamide hydrochloride → L-methyltyrosine (672-87-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen / palladium on carbon / methanol / 1.33 h / 50 °C / 2250.23 Torr 2: hydrogen bromide / water / 4 h / 120 °C View Scheme

C22H26ClNO3 (1299492-17-3) → L-methyltyrosine (672-87-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / isopropyl alcohol; water / 1 h / 20 °C 2: boron tribromide / dichloromethane / 1.5 h / 20 °C View Scheme

2-amino-3-(4-hydroxy-phenyl)-2-methyl-propionic acid (658-48-0) → L-methyltyrosine (672-87-7) + α-methyl-D-tyrosine (672-86-6)

Conditions	Yield
With Merck RP-18 WF254S plates coated with Nτ-n-decyl-L-spinacine and Cu acetate In ethanol; water Resolution of racemate;

N-(benzylidene)-O-methoxymethyl tyrosine tert-butyl ester + methyl iodide (74-88-4) → L-methyltyrosine (672-87-7)

Conditions	Yield
Stage #1: N-(benzylidene)-O-methoxymethyl tyrosine tert-butyl ester; methyl iodide With ((11bS)-(+)-4,4-dibutyl-4,5-dihydro-2,6-bis(3,4,5-triflourophenyl)-3H-dinaphth[2,1-c:1’,2’-e]azepinium bromide); cesium hydroxide In toluene at 0℃; for 0.5h; Inert atmosphere; Stage #2: With hydrogenchloride In water; toluene at 60℃; for 0.5h; Inert atmosphere; stereoselective reaction;	n/a

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + L-methyltyrosine (672-87-7) → Fmoc-L-(α-Me)Tyr-OH (246539-83-3)

Conditions	Yield
With sodium hydroxide In acetonitrile at 20℃; for 3h; Acylation;	100%

methanol (67-56-1) + L-methyltyrosine (672-87-7) → (S)-2-amino-3-(4-hydroxy-phenyl)-2-methyl-propionic acid methyl ester hydrochloride

Conditions	Yield
With thionyl chloride at 0 - 20℃; Heating / reflux;	96%
With thionyl chloride at 0 - 20℃;
With thionyl chloride at 20℃; for 24h; Inert atmosphere; Reflux;	1.48 g

L-methyltyrosine (672-87-7) + n-hexadecanoyl chloride (112-67-4) → N-palmitoyl-α-methyl-L-tyrosine

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 16h;	89%
In N,N-dimethyl-formamide at 20℃; for 16h;	89%

di-tert-butyl dicarbonate (24424-99-5) + L-methyltyrosine (672-87-7) → Boc-(L)(α-Me)Tyr-OH (74825-83-5)

Conditions	Yield
Stage #1: L-methyltyrosine With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine In dichloromethane Inert atmosphere; Stage #2: di-tert-butyl dicarbonate In dichloromethane Inert atmosphere; Stage #3: With methanol for 0.5h; Inert atmosphere;	67%
With sodium hydroxide; sodium hydrogencarbonate In 1,4-dioxane at 20℃; pH=8 - 9;	60%
With sodium hydroxide; tert-butyl alcohol	35%

cis-dichloro(2,2′-bipyridine)ruthenium(II)chloride + L-methyltyrosine (672-87-7) + sodium perchlorate → Ru(N2C10H8)2(NH2CCH3CH2C6H4OHCOO)(1+)*ClO4(1-)*2.5H2O=Ru(N2C10H8)2(NH2CCH3CH2C6H4OHCOO)ClO4*2.5H2O

Conditions	Yield
With sodium hydroxide In ethanol; water Ru-complex was refluxed in mixt. of H2O and EtOH, to this soln. was added ligand followed by aq. NaOH, mixt. was heated at 70°C for 30 min, cooled to room temp., filtered, aq. soln. of NaClO4 was added, mixt.was stored in the dark for 48 h; solid was collected at the pump, washed with ice-cold H2O, dried in vac. over silica gel at room temp.; elem. anal.;	41%

cis-dichloridobis(1,10-phenanthroline)ruthenium(II) + L-methyltyrosine (672-87-7) + sodium perchlorate → Ru(N2C12H8)2(NH2CCH3CH2C6H4OHCOO)(1+)*ClO4(1-)=Ru(N2C12H8)2(NH2CCH3CH2C6H4OHCOO)ClO4

Conditions	Yield
With sodium hydroxide In ethanol; water Ru-complex was refluxed in mixt. of H2O and EtOH, to this soln. was added ligand followed by aq. NaOH, mixt. was heated at 70°C for 30 min, cooled to room temp., filtered, aq. soln. of NaClO4 was added, mixt.was stored in the dark for 48 h; solid was collected at the pump, washed with ice-cold H2O, dried in vac. over silica gel at room temp.; elem. anal.;	39%

L-methyltyrosine (672-87-7) → L-3-18F-α-methyltyrosine + [18F]-3,5-difluoro-L-α-methyltyrosine

Conditions	Yield
With 18F-fluoride In formic acid at 4℃; Product distribution; Further Variations:; Solvents; Temperatures;	A 13% B 2%
With 18F-fluoride; hydrogen fluoride; boron trifluoride

L-methyltyrosine (672-87-7) → 3-iodo-α-methyl-L-tyrosine

Conditions	Yield
With ammonium hydroxide; iodine; potassium iodide

L-methyltyrosine (672-87-7) + benzyl chloroformate (501-53-1) → (S)-N2-<(benzyloxy)carbonyl>-2-methyltyrosine

Conditions	Yield
With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine 1.) CHCl3, 70 deg C, 1 h; 2.) CHCl3, 70 deg C, 1 h; 3.) CHCl3, 80 deg C, 17 h; Yield given. Multistep reaction;

L-methyltyrosine (672-87-7) → L-3-18F-α-methyltyrosine

Conditions	Yield
With 18F-fluoride; hydrogen fluoride

methanol (67-56-1) + L-methyltyrosine (672-87-7) → α-methyl-para-tyrosine methyl ester (7423-78-1)

Conditions	Yield
With thionyl chloride Heating;

L-methyltyrosine (672-87-7) → Boc-(L)(α-Me)Tyr-OMe (675106-56-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 / Heating 2: aq. NaHCO3; NaOH / dioxane / 20 °C / pH 8 - 9 View Scheme

L-methyltyrosine (672-87-7) → Boc-(L)(α-Me)Tyr(Tf)-OMe (675106-57-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: SOCl2 / Heating 2: aq. NaHCO3; NaOH / dioxane / 20 °C / pH 8 - 9 3: 80 percent / Et3N / CH2Cl2 / 3 h / 20 °C View Scheme

L-methyltyrosine (672-87-7) → Boc-(L)(α-Me)Phe(4-PO3Et2)-OMe (675106-58-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: SOCl2 / Heating 2: aq. NaHCO3; NaOH / dioxane / 20 °C / pH 8 - 9 3: 80 percent / Et3N / CH2Cl2 / 3 h / 20 °C 4: 77 percent / Pd(PPh3)4; N-methylmorpholine / acetonitrile / Heating View Scheme

L-methyltyrosine (672-87-7) → Boc-(α-Me)Tyr-Asn-NH2 (675106-63-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / aq. NaHCO3; NaOH / dioxane / 20 °C / pH 8 - 9 2: 86 percent / DIEA; HOAt; HATU / dimethylformamide / 72 h / 20 °C View Scheme

L-methyltyrosine (672-87-7) → (L)(α-Me)Phe(4-PO3H2)-OH*HCl

Conditions	Yield
Multi-step reaction with 5 steps 1: SOCl2 / Heating 2: aq. NaHCO3; NaOH / dioxane / 20 °C / pH 8 - 9 3: 80 percent / Et3N / CH2Cl2 / 3 h / 20 °C 4: 77 percent / Pd(PPh3)4; N-methylmorpholine / acetonitrile / Heating 5: 100 percent / aq. HCl / Heating View Scheme

L-methyltyrosine (672-87-7) → Boc-(α-Me)pTyr(Bzl2)-Asn-NH2 (675106-65-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 60 percent / aq. NaHCO3; NaOH / dioxane / 20 °C / pH 8 - 9 2: 86 percent / DIEA; HOAt; HATU / dimethylformamide / 72 h / 20 °C View Scheme

L-methyltyrosine (672-87-7) → Boc-(α-Me)pTyr(MeSATE)2-Asn-NH2 (675106-64-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 60 percent / aq. NaHCO3; NaOH / dioxane / 20 °C / pH 8 - 9 2: 86 percent / DIEA; HOAt; HATU / dimethylformamide / 72 h / 20 °C View Scheme

L-methyltyrosine (672-87-7) → (α-Me)pTyr-Asn-NH2

Conditions	Yield
Multi-step reaction with 4 steps 1: 60 percent / aq. NaHCO3; NaOH / dioxane / 20 °C / pH 8 - 9 2: 86 percent / DIEA; HOAt; HATU / dimethylformamide / 72 h / 20 °C 3: 93 percent / CH2Cl2 / 3 h / 20 °C View Scheme

L-methyltyrosine (672-87-7) → (α-Me)pTyr(MeSATE)2-Asn-NH2

Conditions	Yield
Multi-step reaction with 4 steps 1: 60 percent / aq. NaHCO3; NaOH / dioxane / 20 °C / pH 8 - 9 2: 86 percent / DIEA; HOAt; HATU / dimethylformamide / 72 h / 20 °C 3: CH2Cl2 / 1 h / 0 °C View Scheme

Upstream product

• 65555-88-6 α-methyl-β-p-methoxyphenyl-alanine 
• 121703-96-6 N-Chloroacetyl-α-methyltyrosine 
• 74-88-4 methyl iodide 
• 658-48-0 2-amino-3-(4-hydroxy-phenyl)-2-methyl-propionic acid 
• 1299492-20-8 (2S)-2-amino-3-(4-methoxyphenyl)-2-methylpropionamide formic acid salt 
• 1299492-19-5 (2S)-2-amino-3-(4-methoxyphenyl)-2-methyl-propionamide hydrogen bromide salt 
• 1299492-17-3 C₂₂H₂₆ClNO₃ 
• 1299492-14-0 (2S)-2-amino-3-(4-methoxyphenyl)-2-methyl-propionamide hydrochloride 
• 1299492-12-8 3-(4-methoxyphenyl)-2-methyl-2-((1S)-1-phenyl-ethylamino)-propionamide hydrochloride 
• 1299492-11-7 3-(4-methoxyphenyl)-2-methyl-2-((S)-1-phenyl-ethylamino)-propionamide 
• 1299492-09-3 2-(S)-amino-3-(4-methoxyphenyl)-2-methylpropionamide 
• 1299492-08-2 2-[(R)-(carbamoylphenylmethyl)-amino]-3-(4-methoxyphenyl)-2-(S)-methylpropionamide 
• 1299492-07-1 2-[1-(S)-cyano-2-(4-methoxyphenyl)-1-methylethylamino]-2-(R)-phenylacetamide 
• 122-84-9 4-methoxybenzyl methyl ketone 

Downstream Products

• 7423-78-1 α-methyl-para-tyrosine methyl ester 
• 675106-56-6 Boc-(L)(α-Me)Tyr-OMe 
• 675106-57-7 Boc-(L)(α-Me)Tyr(Tf)-OMe 
• 675106-58-8 Boc-(L)(α-Me)Phe(4-PO3Et2)-OMe 
• 675106-63-5 Boc-(α-Me)Tyr-Asn-NH2 
• 675106-65-7 Boc-(α-Me)pTyr(Bzl2)-Asn-NH2 
• 675106-64-6 Boc-(α-Me)pTyr(MeSATE)2-Asn-NH2 
• 658-48-0 2-amino-3-(4-hydroxy-phenyl)-2-methyl-propionic acid 

Relevant articles and documents

METHOD FOR PRODUCING AMINO ACID AND AMINO ACID SYNTHESIS KIT

PROBLEM TO BE SOLVED: To provide a method for producing an amino acid and an amino acid synthesis kit, which enable synthesis of a desired amino acid in high stereoselectivity efficiently and in a very short time, irrespective whether a radioactive isotope is contained or not. SOLUTION: A method for producing an amino acid and an amino acid synthesis kit are disclosed. The method for producing an amino acid of the present invention comprises a step of alkylating a substrate compound with an alkylating agent in the presence of an optically active phase transfer catalyst as well as a medium and an inorganic base. An amount of use of the optically active phase transfer catalyst is 1 equivalent or more and 1000 equivalents or less relative to the alkylating agent. According to the present invention, a desired amino acid and a derivative thereof can be produced in high stereoselectivity efficiently and in a very short time. Therefore, the present production method is useful, for example, for research and development, and production of a radioactively labelled amino acid and a derivative thereof, which can be used as a tracer for neurodegenerative diseases such as Parkinson disease and Alzheimer disease, heart diseases, and cancerous diseases. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

STEREOSELECTIVE SYNTHESIS OF METYROSINE

Provided herein are compositions including diastereomers in substantially diastereomerically pure form and enantiomers in substantially enantiomerically pure form, and processes for preparing them and converting them to metyrosine.

Kinetic Resolution of Unnatural and Rarely Occuring Amino Acids: Enantioselective Hydrolysis of N-Acyl Amino Acids Catalyzed by Acylase I

Acylase I (aminoacylase; N-acylamino-acid amidohydrolase, EC 3.5.1.14, from porcine kidney and the fungus Aspergillus) is broadly applicable enzymatic catalyst for the kinetic resolution of unnatural and rarely occuring α-amino acids.Its enantioselectivity for the hydrolysis of N-acyl L-α-amino acids is nearly absolute, yet it accepts substrates having a wide range of structure and functionality.This paper reports the initial rates of enzyme-catalyzed hydrolysis of over 50 N-acyl amino acids and analogues, the stabilities of the enzymes in aqueous and aqueous/organic solutions, and the effects of different acyl groups and metal ions on the rates of enzymatic hydrolysis.Eleven α-amino and α-methyl α-amino acids were resolved on a 2-29-g scale.Crude L- and D-amino acid products had generally >90percent ee.The utility of resolved amino acids as chiral synthons was illustrated by the preparation of (R)- and (S)-1-butene oxide and the diastereoselective (cis:trans, 7-8:1) iodolactonization of three 2-amino-4-alkenoic acid derivatives.