219909-83-8

Basic information

• Product Name: 3-[(2S,4S)-4-Mercaptopyrrolidine-2-carboxamido]benzoic acid hydrochloride
• Synonyms: THIAPROLINE-M-AMINO-BENZOIC ACID HYDROCHLORIDE;3-((4S)-4-SULFANYL-L-PROLINAMIDOL)BENZOZUURHYDROCHLORIDE;(2S)-2-cis-3-[[4-Mercapto-2-pyrrolidinyl)carbonyl]amino]benzoic acid hydrochloride;3-[(2S,4S)-4-Mercaptopyrrolidine-2-carboxamido]benzoic acid hydrochloride;SIDECHAINIIFORERTAPENEM;3-[(2S,4S)-4-Mercaptopyrrolidine-2-carboxamido]benzoic;3-[[[(2S, 4S)-4-mercapto-1-[(4-nitrobenzyloxy)carbonyl]-2-pyrrolidinyl]carbonyl]amino]-(4-nitrobenzyl)benzoate;3-[(2S,4S)-4-Mercaptopyrrolidine-2-carboxaMido]benzoic acid hcl
• CAS NO: 219909-83-8
• Molecular Formula: C12H15ClN2O3S
• Molecular Weight: 302.78
• EINECS: 1308068-626-2
• Mol File: 219909-83-8.mol

Chemical Properties

• Melting Point: 212 °C
• Boiling Point: 564.1 °C at 760 mmHg
• Flash Point: 295 °C
• Appearance: /
• Vapor Pressure: 1.46E-13mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly), Phosphoric Acid (Slightly), Water (Slightl
• CAS DataBase Reference: 3-[(2S,4S)-4-Mercaptopyrrolidine-2-carboxamido]benzoic acid hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[(2S,4S)-4-Mercaptopyrrolidine-2-carboxamido]benzoic acid hydrochloride(219909-83-8)
• EPA Substance Registry System: 3-[(2S,4S)-4-Mercaptopyrrolidine-2-carboxamido]benzoic acid hydrochloride(219909-83-8)

Safety Data

• Hazardous Substances Data: 219909-83-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-[(2S,4S)-4-Mercaptopyrrolidine-2-carboxamido]benzoic acid hydrochloride is used as a key reactant in the synthesis of carbapenem antibiotics, specifically Ertapenem Sodium. Its unique structure and reactivity contribute to the formation of the antibiotic's core structure, which is essential for its broad-spectrum antibacterial activity.
Ertapenem Sodium, a carbapenem antibiotic, is known for its effectiveness against a wide range of Gram-negative and Gram-positive bacteria, making it a valuable asset in treating various infections. The synthesis of this antibiotic relies on the properties of 3-[(2S,4S)-4-Mercaptopyrrolidine-2-carboxamido]benzoic acid hydrochloride, highlighting its importance in the development of life-saving medications.

InChI:InChI=1/C12H14N2O3S.ClH/c15-11(10-5-9(18)6-13-10)14-8-3-1-2-7(4-8)12(16)17;/h1-4,9-10,13,18H,5-6H2,(H,14,15)(H,16,17);1H/t9-,10-;/m0./s1

Upstream product

• 99-05-8 meta-aminobenzoic acid 
• 96034-57-0 (2S,4R)-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid 
• 51-35-4 4R-4-hydroxyproline 
• 202467-69-4 (2S,4S)-2-[[(3-carboxyphenyl)amino]carbonyl]-4-mercapto-1-(4-nitrobenzyl)pyrrolidine carboxylate 
• 266337-24-0 C₂₄H₃₃NO₉P₂S 
• 266337-23-9 (2S-trans)-1-[bis(1-methylethoxy)phosphinyl]tetrahydro-4-hydroxy-2H-pyrrole-2-carboxylic acid diphenylphosphinyl ester 
• 220030-10-4 (1S)-(3-oxo-2-thio-5-azabicyclo[2.2.1]hept-5-yl)phosphonic acid bis(1-methylethyl) ester 
• 117286-92-7 N‐(O,O‐diisopropylphosphoryl)-trans-4‐hydroxy-L-proline 
• 220031-86-7 3-{[(2S,4S)-1-(Diisopropoxy-phosphoryl)-4-mercapto-pyrrolidine-2-carbonyl]-amino}-benzoic acid 

Relevant articles and documents

Efficient one-pot synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio-containing side chain of the new broad-spectrum carbapenem antibiotic ertapenem.

An efficient synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio containing side chain of ertapenem (MK-0826) is described. Starting material N-(O,O-diisopropyl phosphoryl)-trans-4-hydroxy-L-proline is converted in a one-pot process to (2S)-cis-3-[[(4-mercapto-2-pyrrolidinyl)carbonyl]amino]benzoic acid monohydrochloride in 70-75% overall yield via a series of six reactions. The development of each of these reactions and the isolation of the product is discussed in detail.

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.

Novel preparation method of ertapenem side chain

The invention relates to an innovation-type preparation method of an ertapenem side chain (represented by the formula 1). The method comprises the steps: (1) with amino protected thiolactone (represented by the formula I) as a raw material, under an acidic condition, with SiO2 and gamma-Al2O3 as carriers, and with a catalyst prepared with palladium as an active ingredient, carrying out a hydrogenation deprotection reaction, to obtain deprotected thiolactone (represented by the formula 2); and (2) carrying out a reaction of the compound 2 and m-aminobenzoic acid, to obtain the target compound (represented by the formula 1). With easily-available, relatively-inexpensive and amino protected thiolactone having a mature preparation process as the raw material, the improved palladium catalyst is innovatively used for hydrogenation deprotection, the compound 2 is obtained, and then the compound 2 is subjected to a reaction with m-aminobenzoic acid to prepare the target compound; the preparation method has the advantages of cheap and easily available raw materials, high product yield, low production cost, economy, safety and environmental protection, and is more suitable for industrialized production.