1192651-49-2

Basic information

• Product Name: (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
• Synonyms: (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;(1R,2S,5R)-7-Oxo-6-(phenylmethoxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;(1R,2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
• CAS NO: 1192651-49-2
• Molecular Formula: C₁₄H₁₇N₃O₃
• Molecular Weight: 275.30308
• EINECS: -0
• Mol File: 1192651-49-2.mol

Chemical Properties

• Boiling Point: 543.6±30.0 °C(Predicted)
• Appearance: /
• Density: 1.36±0.1 g/cm3(Predicted)
• PKA: 17.19±0.20(Predicted)
• CAS DataBase Reference: (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide(1192651-49-2)
• EPA Substance Registry System: (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide(1192651-49-2)

Safety Data

• Hazardous Substances Data: 1192651-49-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 1192651-49-2 differently. You can refer to the following data:
1. (2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide is an impurity of Avibactam; a novel β-lactamase inhibitor with a non-lactam structural scaffold. Avibactam irreversibly inhibits lactamase from Mycobacterium tuberculosis.
2. (2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide is an impurity of Avibactam (A794850, Na Salt); a novel β-lactamase inhibitor with a non-lactam structural scaffold. Avibactam irreversibly inhibits lactamase from Mycobacterium tuberculosis.

Upstream product

• 1174020-25-7 (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid 
• 1383814-57-0 (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid cyclohexylamine salt 
• 1383814-55-8 (2S,5R)-tert-butyl 5-(benzyloxyamino)piperidine-2-carboxylate 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 1416134-49-0 (2S,5R)-5-(benzyloxyamino)-piperidine-2-carboxylic acid amide 
• 32159-21-0 Cbz-L-pGlu-OH 
• 1383814-53-6 (2S,5S)-tert-butyl 5-hydroxy-1-(2,2,2-trifluoroacetyl)piperidine-2-carboxylate 
• 1383814-52-5 (2S,5S)-tert-butyl 5-hydroxypiperidine-2-carboxylate 
• 169825-97-2 N-benzyloxycarbonyl-(2S,5S)-5-hydroxypipecolic acid tert-butyl ester 
• 1383814-60-5 (2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid 2,5-dioxopyrrolidin-1-yl ester 
• 1383814-58-1 (2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid methyl ester 
• 1383814-56-9 (2S,5R)-tert-butyl 6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate 
• 1383814-54-7 (2S,5R)-tert-butyl 5-(benzyloxyamino)-1-(2,2,2-trifluoroacetyl)piperidine-2-carboxylate 

Downstream Products

• 1383814-64-9 (2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 
• 1192651-80-1 ({[(2S,5R)-2-carbamoyl-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3,2,1]-oct-6-yl]oxy}sulfonyl)tetrabutylammonium salt 
• 1192491-61-4 (2S,5R)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 7-oxo-6-(sulfoxy)monosodium salt 
• 1192500-31-4 (2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicylco[3.2.1]octan-6-yl hydrogensulfate 
• 1471297-88-7 (2S,5R)-6-(benzyloxy)-2-(1,2,4-oxadiazol-5-yl)-1,6-diazabicyclo[3.2.1]octan-7-one 
• 1471297-86-5 (2S,5R,Z)-6-(benzyloxy)-N-((dimethylamino)methylene)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 

Relevant articles and documents

Preparation method of avibactam sodium

The invention discloses a synthesis method of avibactam sodium. (2S,5R)-benzyloxyamino piperidine-2-ethyl formate oxalate (I) is used as an initial raw material; and the method comprises the followingsteps: reacting the raw material with a protecting group, carrying out carbonylation cyclization, carrying out hydrolysis of ester, ammoniating, sulfonating with a sulfur trioxide complex, salifyingwith an ammonium ion source, and salifying with a sodium salt to obtain avibactam sodium, and has the advantages of simple operation, easily controlled conditions, easy industrial production and wideapplication prospect.

Simple and convenient preparation method of avibatan intermediate

The invention discloses a simple and convenient preparation method of an avibatan intermediate. The simple and convenient preparation method of the avibatan intermediate includes the steps that a typeIII compound is taken as a raw material, hydrolyzed under the alkaline condition, and then acidized to prepared a type IV compound, the obtained type IV compound and striphosgene or diphosgene are subjected to cyclic urea and acylating chlorination reactions simultaneously in the presence of an organic base and a catalyst, a type V compound is obtained, and a final product (II) is then obtained after amidation. According to the simple and convenient preparation method of the avibatan intermediate, the cyclic urea, acylating chlorination and amidation reactions are completed by a 'one pot method', and intermediate products do not need to be separated and purified; and raw materials are cheap and easy to get, the process is simple, operability is high, no special protective agent and carbonylation reagent are required, the reaction atom economical efficiency is high, the cost is low, the production process is environment friendly, the purity of the obtained product (II) is high, the yield is high, and cost reduction and environment-friendly production of an avibatan (I) is facilitated.

Avibactam intermediate and preparation method thereof

The invention provides a method for preparing a compound 3. The preparation method comprises the following steps: 1) carrying out an amino protection reaction on a compound I to obtain a compound II;2) carrying out an amidation reaction on the compound II to obtain a compound III; and 3) carrying out a cyclization reaction on the compound III to obtain the compound 3. The invention also disclosesan intermediate compound II, which can be used for preparing the compound 3 and avibactam.

A synthesis method of avey batanbatan sodium (by machine translation)

The invention discloses a method for synthesizing avey batanbatan sodium. The current method for synthesizing method, the production cost is higher; intermediate reduction of low selectivity, leading to reduced yield; at the same time the reaction by-products created in toxicity is relatively large, not friendly to the environment and other factors also limits the large-scale production. The invention relates to 5 - hydroxy - 2 - pyridine carboxylic acid ethyl ester as the starting material, reduction and hydrogenation, biological lipase split, electrophilic addition, nucleophilic substitution, de-Boc, aminolysis, intramolecular immortal, debenzylation, sulfonic ester, salt and cation exchange a total of 11 obtain avey batanbatan sodium. Synthesis method of the invention has high yield, route is brief, mild reaction conditions, small pollution to the environment, it is easy to large-scale preparation and the like. (by machine translation)

Strategic Approaches to Overcome Resistance against Gram-Negative Pathogens Using β-Lactamase Inhibitors and β-Lactam Enhancers: Activity of Three Novel Diazabicyclooctanes WCK 5153, Zidebactam (WCK 5107), and WCK 4234

Limited treatment options exist to combat infections caused by multidrug-resistant (MDR) Gram-negative bacteria possessing broad-spectrum β-lactamases. The design of novel β-lactamase inhibitors is of paramount importance. Here, three novel diazabicyclooctanes (DBOs), WCK 5153, zidebactam (WCK 5107), and WCK 4234 (compounds 1-3, respectively), were synthesized and biochemically characterized against clinically important bacteria. Compound 3 inhibited class A, C, and D β-lactamases with unprecedented k2/K values against OXA carbapenemases. Compounds 1 and 2 acylated class A and C β-lactamses rapidly but not the tested OXAs. Compounds 1-3 formed highly stable acyl-complexes as demonstrated by mass spectrometry. Crystallography revealed that 1-3 complexed with KPC-2 adopted a "chair conformation" with the sulfate occupying the carboxylate binding region. The cefepime-2 and meropenem-3 combinations were effective in murine peritonitis and neutropenic lung infection models caused by MDR Acinetobacter baumannii. Compounds 1-3 are novel β-lactamase inhibitors that demonstate potent cross-class inhibition, and clinical studies targeting MDR infections are warranted.

RETRACTED ARTICLE: A New Synthetic Route to Avibactam: Lipase Catalytic Resolution and the Simultaneous Debenzylation/Sulfation

An efficient synthesis of avibactam starting from commercially available ethyl-5-hydroxypicolinate was completed in 10 steps and 23.9% overall yield. The synthesis features a novel lipase-catalyzed resolution, in the preparation of (2S,5S)-5-hydroxypiperidine-2-carboxylate acid, which is a valuable precusor of the key intermediate ethyl (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate. An optimized one-pot debenzylation/sulfation reaction, followed by cation exchange, gave the avibactam sodium salt on a 400.0 g scale.

Use of Lipase Catalytic Resolution in the Preparation of Ethyl (2 S,5 R)-5-((Benzyloxy)amino)piperidine-2-carboxylate, a Key Intermediate of the β-Lactamase Inhibitor Avibactam

Here we describe an efficient and cost-effective chemoenzymatic synthesis of the β-lactamase inhibitor avibactam starting from commercially available ethyl 5-hydroxypicolinate hydrochloride. Avibactam was synthesized in 10 steps with an overall yield of 23.9%. The synthetic route features a novel lipase-catalyzed resolution step during the preparation of (2S,5S)-ethyl 5-hydroxypiperidine-2-carboxylate, a valuable precursor of the key intermediate ethyl (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate. Our synthetic route was used to produce 400 g of avibactam sodium salt.

Preparation methods of sodium avibactam and intermediate compound thereof

The invention provides a preparation method of sodium avibactam. The method comprises that sodium 2-ethylhexanoate reacts with an intermediate compound K, so that the sodium avibactam is obtained. Theinvention also provides a preparation method of the intermediate compound K. The preparation method comprises the following steps: (1) carrying out reaction on a compound J with ammonium formate, formic acid and triethylamine in presence of a catalyst, and removing benzyl, so that a compound K1 is obtained; (2) adding an acid binding agent, a sulfonation reagent and water into the K1 reaction liquid obtained in the step (1), and reacting; and (3) adding tetrabutylammonium acetate aqueous solution into the reaction liquid obtained in the step (2), stirring and reacting, then adding an extraction solvent, separating out an organic phase, drying, then distilling off the solvent, adding a crystallization solvent, stirring, and crystallizing, so that the compound K is obtained. The preparationmethods provided by the invention are low in cost, avoid a high-risk preparation method for debenzylation through hydrogenation, are high in safety performance, easy to operate and applicable to industrial production and have greater application value.

Preparation method of Avibactam intermediate

The invention relates to a preparation method of an Avibactam intermediate. The intermediate is (1R, 2S, 5R)-6-benzyloxy-7-oxo-1,6-diazacyclo[3.2.1]octane-2-methanamide. The method is easy to implement; total yield is high; purity of the product obtained is high; and the product is easy to purify.

One-pot method of preparing avey batanBatan sodium (by machine translation)

The invention discloses a method for preparing avey batanBatan sodium pot method. The method to (2S, 5R) - 5 - [(benzyloxy) amino] piperidine - 2 - carboxylic acid ethyl ester oxalate as the starting material first with triphosgene generating compounds II, then after hydrolysis to obtain compound III ammoniation of adding ammonia water, then in hydrogenation reaction using formic acid, ammonium formate or hydrazine hydrate as hydrogen donor hydrogenation after avey batanBatan sodium and get. The method adopts the one-pot preparation avey batanBatan sodium, and the raw material is cheap, mild reaction conditions, the operation is simple, and higher safety, high yield, purity is good, is suitable for the large-scale industrial production. (by machine translation)