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

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

Used in Pharmaceutical Industry:
3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid is used as a key intermediate in the synthesis of Ertapenem (E635000), a broad-spectrum antibiotic belonging to the carbapenem class. It is effective against a wide range of Gram-negative and Gram-positive bacteria, including those resistant to other antibiotics. 3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid plays a vital role in the development of new antimicrobial agents to combat drug-resistant infections.
Additionally, this compound may also be utilized in the synthesis of other related intermediates, which could further contribute to the development of novel pharmaceuticals with improved properties or alternative applications in the medical field. Its unique structure and reactivity make it a valuable component in the design and synthesis of advanced drug candidates.

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

• 51-35-4 4R-4-hydroxyproline 
• 96034-57-0 (2S,4R)-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid 
• 4457-32-3 4-nitrobenzyl chloroformate 
• 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 
• 1262305-54-3 C₄₄H₄₀N₆O₁₅S 
• 153832-46-3 ertapenem 
• 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 

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.

Improved manufacturing method of ertapenem side chain

The invention relates to an improved preparation method of a carbapenem compound ertapenem side chain (disclosed as Formula 1). The method comprises the following step: by using amino-protected thiolactone (disclosed as Formula I) as a raw material, carrying out reaction with 3-aminobenzoic acid under acidic conditions by using single saturated alcohol as a reaction solvent, thereby preparing the target compound. By using the single saturated alcohol as the reaction solvent, the crystal characters of the product are improved, and the production cycle is shortened. The method is economical, safe and environment-friendly, and is more suitable for the industrial production scale.

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).