1416134-73-0

Basic information

• Product Name: (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate methyl ester
• CAS NO: 1416134-73-0
• Molecular Weight: 264.324
• Mol File: 1416134-73-0.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 377.5±52.0 °C(Predicted)
• Density: 1.15±0.1 g/cm3(Predicted)
• CAS DataBase Reference: (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate methyl ester(1416134-73-0)
• EPA Substance Registry System: (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate methyl ester(1416134-73-0)

Safety Data

• Hazardous Substances Data: 1416134-73-0(Hazardous Substances Data)

Usage

Description

(2S,5R)-5-((Benzyloxy)amino)piperidine-2-carboxylate methyl ester is an organic compound with a unique molecular structure, characterized by its stereochemistry at the 2S and 5R positions. It features a benzyloxyamino group attached to the piperidine ring and a carboxylate group at the 2-position, with a methyl ester functional group. (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate methyl ester is known for its potential applications in the pharmaceutical industry, particularly as an impurity in the synthesis of certain drugs.

Uses

Used in Pharmaceutical Industry:
(2S,5R)-5-((Benzyloxy)amino)piperidine-2-carboxylate methyl ester is used as an impurity in the synthesis of Avibactam, a novel β-lactamase inhibitor with a non-lactam structural scaffold. Avibactam is known for its irreversible inhibition of lactamase from Mycobacterium tuberculosis, making it a valuable compound in the development of new antibiotics to combat drug-resistant bacterial infections.
In the development of new drugs, the presence of impurities like (2S,5R)-5-((Benzyloxy)amino)piperidine-2-carboxylate methyl ester can be crucial for understanding the synthesis process, optimizing the production, and ensuring the safety and efficacy of the final product. By studying the properties and behavior of this compound, researchers can gain insights into the drug's mechanism of action, potential side effects, and ways to improve its performance.

Upstream product

• 1487347-86-3 (2S,5S)-N-tert-butoxycarbonyl-5-hydroxy-2-carboxylic acid piperidine 
• 1033774-90-1 N-4-nitrobenzene sulfonyl-O-benzylhydroxylamine 
• 67-56-1 methanol 
• 7647-01-0 hydrogenchloride 
• 68-11-1 mercaptoacetic acid 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 77925-80-5 N-(2-Nitrophenylsulfonyl)-O-(phenylmethyl)hydroxylamine 
• 915976-32-8 (2S,5S)-1-tert-butyl 2-methyl 5-hydroxypiperidine-1,2-dicarboxylate 
• 915976-31-7 1-(tert-butyl) 2-methyl (S)-5-oxopiperidine-1,2-dicarboxylate 
• 108963-96-8 (S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one 
• 56-86-0 L-glutamic acid 

Downstream Products

• 1383814-58-1 (2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid methyl ester 
• 1174020-25-7 (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid 
• 1426572-71-5 (2S,5R)-N’-acetyl-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide 
• 1452467-32-1 (2S,5R)-6-(benzyloxy)-7-oxo-N’-propanoyl-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide 
• 1452466-57-7 (2S,5R)-6-(benzyloxy)-N-methoxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 
• 1452466-19-1 {2-[({[(2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]ethyl}carbamic acid tert-butyl ester 
• 1452458-86-4 RG₆₀₈₀ 
• 1426573-07-0 (2S,5R)-1-[(1,1-dimethylethyl)carbonyl]-5-[(benzyloxy)amino]piperidine-2-carboxylic acid 
• 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 
• 1452465-83-6 (3S)-3-[({[(2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]pyrrolidin-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

METHOD FOR PRODUCING AMINO ACID DERIVATIVES

The present invention aims to provide a method for producing a (2S,5R)-5-(protected oxyamino)-piperidine-2-carboxylic acid derivative at a low cost that can be performed under mild reaction conditions not requiring a facility at an extremely low temperature, is safer, can control the quality of the desired product with ease, and shows good workability in the site of production. A method for producing a compound represented by the formula (2): wherein PG1 is an amino-protecting group, PG2 is an amino-protecting group, PG3 is a hydroxyl-protecting group, LG is a leaving group, and R is a hydrocarbon group having 1-8 carbon atoms and optionally having substituent(s), including a step of reacting a compound represented by the formula (1): wherein each symbol is as defined above, with a hydroxylamine derivative represented by the formula PG2NHOPG3 wherein each symbol is as defined above, in the presence of a base in a solvent.

NEW BETA-LACTAMASE INHIBITORS TARGETING GRAM NEGATIVE BACTERIA

The present invention relates to a compound of the following formula (I) or a pharmaceutically acceptable salt and/or solvate thereof, notably for use as β-lactamase inhibitors, notably in the treatment of a disease caused by gram negative bacteria, in particular enterobacteria, as well as pharmaceutical compositions containing such a compound and a process to prepare such a compound.

Synthesis of Avibactam Derivatives and Activity on β-Lactamases and Peptidoglycan Biosynthesis Enzymes of Mycobacteria

There is a renewed interest for β-lactams for treating infections due to Mycobacterium tuberculosis and M. abscessus because their β-lactamases are inhibited by classical (clavulanate) or new generation (avibactam) inhibitors, respectively. Here, access to an azido derivative of the diazabicyclooctane (DBO) scaffold of avibactam for functionalization by the Huisgen–Sharpless cycloaddition reaction is reported. The amoxicillin–DBO combinations were active, indicating that the triazole ring is compatible with drug penetration (minimal inhibitory concentration of 16 μg mL?1 for both species). Mechanistically, β-lactamase inhibition was not sufficient to account for the potentiation of amoxicillin by DBOs. Thus, the latter compounds were investigated as inhibitors of l,d-transpeptidases (Ldts), which are the main peptidoglycan polymerases in mycobacteria. The DBOs acted as slow-binding inhibitors of Ldts by S-carbamoylation indicating that optimization of DBOs for Ldt inhibition is an attractive strategy to obtain drugs selectively active on mycobacteria.