87657-41-8

Usage

Uses

Used in Pharmaceutical Industry:
(3S)-3-Mercapto-(4-nitrophenyl)methylester-1-pyrrolidinecarboxylic acid is used as a key intermediate in the synthesis of Panipenem (P180000) for its broad-spectrum antibacterial and antimicrobial properties. It is effective against both Gram-negative and Gram-positive organisms, making it a valuable component in the development of new antibiotics to combat drug-resistant infections.

Upstream product

• 181960-38-3 (S)-3-benzoylthio-N-(p-nitrobenzyloxycarbonyl)pyrrolidine 
• 91319-85-6 3-(R)-methanesulfonyloxy-1-p-nitrobenzyloxycarbonylpyrrolidine 
• 105601-88-5 (3R)-3-hydroxy-1-(4-nitrobenzyloxycarbonyl)-pyrrolidine 
• 91319-84-5 3-(S)-acetylthio-1-p-nitrobenzyloxycarbonylpyrrolidine 
• 4457-32-3 4-nitrobenzyl chloroformate 

Downstream Products

• 90629-00-8 (S)-3-(2-Trimethylsilanyl-acetylsulfanyl)-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester 
• 90652-16-7 (S)-3-(2-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-acetylsulfanyl)-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester 
• 101151-51-3 (4R,5S,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3-[(S)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 

Relevant academic research and scientific papers

AN IMPROVED PROCESS FOR THE PREPARATION OF CARBAPENEM ANTIBIOTIC

The present invention relates to an improved process for the preparation of the carbapenem antibiotic of formula (I) or its salts, hydrates and esters. The present invention further provides novel crystalline form of compound of general formula (III), wherein R3 is p-nitrobenzyloxy carbonyl.

PENEM DERIVATIVES AND ANTIMICROBIAL AGENT CONTAINING THE SAME

A penem derivative represented by the following formula (I): wherein R1represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted alkenylthio group, a substituted or unsubstituted aralkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic thio group, a substituted or unsubstituted acylthio group, a mercapto group or a hydrogen atom, and R2represents a hydrogen atom or a carboxyl-protecting group; or a pharmacologically acceptable salt thereof. The compound (I) exhibits strong antibacterial activities, and especially, shows strong activities against MRSA. It is therefore useful not only as a general antibacterial agent but also as an antibacterial agent for MRSA against which no general antibacterial agents are recognized to be effective.

SYNTHESIS OF OPTICALLY ACTIVE 3-MERCAPTOPYRROLIDINE DERIVATIVES. SYNTHETIC INTERMEDIATES OF CARBAPENEM RS-533 AND ITS ISOMER

The optically active 3-mercaptopyrrolidine derivatives(3a, 3b, 4a and 4b), which are synthetic intermediates of the carbapenem RS-533 (2a) and its isomer (2b), were synthesized by convenient and practical methods.