202467-69-4

Basic information

• Product Name: 3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid
• Synonyms: 3-([[(2S,4S)-4-Mercapto-1-((4-nitrobenzyloxy)carbonyl)pyrrolidin-2-yl]carbonyl]aMino)benzoic acid;Ertapenem side chain, Side chain for Ertapenem;Ertapenem side chains;[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid;Side Train of Ertapenem;2-[[(3-Carboxyphenyl)amino]carbonyl]-4-mercapto-1-pyrrolidinecarboxylic acid (2S-cis)-1-[(4-nitrophenyl)methyl] ester;3-[[[(2s,4s)-4-mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid;3-[[[(2S,4S)-4-MERCAPTO-2-PYRROLIDINYL-1-(4-NITROBENZYLOXY)CARBONYL]CARBONYL]AMINO]BENZOIC ACID
• CAS NO: 202467-69-4
• Molecular Formula: C₂₀H₁₉N₃O₇S
• Molecular Weight: 445.45
• EINECS: 1308068-626-2
• Mol File: 202467-69-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 749.6 °C at 760 mmHg
• Flash Point: 407.1 °C
• Appearance: /
• Density: 1.5g/cm³
• Vapor Pressure: 1.33E-23mmHg at 25°C
• Refractive Index: 1.675
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.06±0.10(Predicted)
• CAS DataBase Reference: 3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid(202467-69-4)
• EPA Substance Registry System: 3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid(202467-69-4)

Safety Data

• Hazardous Substances Data: 202467-69-4(Hazardous Substances Data)

Usage

Uses

3-[[[(2S,4S)-1-(4-Nitrobenzyloxycarbonyl)-4-mercaptopyrrolidin-2-yl]carbonyl]amino]benzoic Acid is an intermediate in the preparation of Ertapenem (E635000) and intermediates.

InChI:InChI=1/C20H19N3O7S/c24-18(21-14-3-1-2-13(8-14)19(25)26)17-9-16(31)10-22(17)20(27)30-11-12-4-6-15(7-5-12)23(28)29/h1-8,16-17,31H,9-11H2,(H,21,24)(H,25,26)/t16-,17-/m0/s1

Upstream product

• 4457-32-3 4-nitrobenzyl chloroformate 
• 96034-57-0 (2S,4R)-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid 
• 51-35-4 4R-4-hydroxyproline 
• 99-05-8 meta-aminobenzoic acid 
• 151072-00-3 (2S,4S)-5-p-nitrobenzyloxycarbonyl-2-thia-5-azabicyclo<2.2.1>heptan-3-one 

Downstream Products

• 219909-83-8 (2S-cis)-3-[[(4-mercapto-2-pyrrolidinyl)carbonyl]amino]benzoic acid monohydrochloride 
• 202467-70-7 (4-nitrophenyl)methyl (4R,5S,6S)-3-[[(3S,5S)-5-[[(-carboxyphenyl)amino]carbonyl]-1-[[(4-nitrophenyl)methyoxy]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 
• 1228544-12-4 3-((2S,4S)-1-((4-nitrobenzyloxy)carbonyl)-4-(tritylthio)pyrrolidine-2-carboxamido)benzoic acid 
• 866186-68-7 6-[5-(3-carboxy-phenylcarbamoyl)-pyrrolidin-3-ylsulfanyl]-3,5-dimethyl-1-oxo-3,4,4a,5-tetrahydro-pyrrolo[1,2-c][1,3]oxazine-4,7-dicarboxylic acid 
• 1262305-54-3 C₄₄H₄₀N₆O₁₅S 
• 153832-46-3 ertapenem 

Relevant articles and documents

A luer Ertapenem, luer he lateral chain and its preparation method

The invention discloses ertapenem and ertapenem side chains, as well as preparation methods of ertapenem and ertapenem side chains. L-hydroxyproline is protected by p-nitrobenzyl ester to obtain (2S,4R)-4-hydroxyl-1-(((4-Nitrobenzformyl)-oxyl)caboyl)pyrrolidine-2-carboxylic acid; then 4-nitro(1S,4S)-3-oxo-2-thia-5-azabicyclo[2.2.1]heptan-5-carboxylic anhydride can be obtained, and reacts with m-aminobenzoic acid p-nitrobenzyl ester to obtain ertapenem side chain III; and the ertapenem can be synthesized through two-step chemical reaction of condensation and deprotection to the ertapenem side chain III and a raw material MAP. An ertapenem side chain I (10), an ertapenem side chain II (13) and the ertapenem side chain III (2) which are prevailing in the market can be synthesized through simple steps, without the need of ultralow temperature, industrialization is easy, and the product purity is high, and the operation is simple and convenient.

PROCESS FOR SYNTHESIZING CARBAPENEM ANTIBIOTICS

A process for synthesizing a coumpond of formula (I) or a pharmaceutically acceptable salt or ester thereof, wherein each P independently represents H or a protecting group, and R and R independently represent H, C1-10 alkyl, aryl or heteroaryl, or substituted C1-10 alkyl, aryl or heteroaryl, comprising: reacting the compounds (II) or a pharmaceutically acceptable salt or ester thereof, and (III) or a pharmaceutically acceptable salt or ester thereof, wherein X represents OP(O)(OR)2, or OSO2R, wherein R represents C1-6 alkyl, aryl or perfluoro C1-6 alkyl, in the presence of an amine selected from the group consisting of: diisopropylamine (DIPA), dicyclohexylamine (DCHA), 2,2,6,6-tetramethylpiperidine (TMP), 1,1,3,3-tetramethylguanidine (TMG), 1,8-diazabicyclo[4.3.0]undec-7-ene (DBU) and 1,5-diazabicyclo[4.3.0]non-5-ene to produce a compound of formula (I).