444057-64-1

Basic information

• Product Name: 3,3'-[Dithiobis[(2S,4S)-4,2-pyrrolidinediylcarbonyliMino]]bisbenzoic Acid Dihydrochloride
• Synonyms: (2S)-cis-3-[[(4-Mercapto-2-pyrrolidinyl)carbonyl]aMino]benzoic Acid Disulfide Dihydrochloride;3,3'-[Dithiobis[(2S,4S)-4,2-pyrrolidinediylcarbonyliMino]]bisbenzoic Acid Dihydrochloride
• CAS NO: 444057-64-1
• Molecular Formula: C24H28Cl2N4O6S2
• Molecular Weight: 603.53832
• Mol File: 444057-64-1.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,3'-[Dithiobis[(2S,4S)-4,2-pyrrolidinediylcarbonyliMino]]bisbenzoic Acid Dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3'-[Dithiobis[(2S,4S)-4,2-pyrrolidinediylcarbonyliMino]]bisbenzoic Acid Dihydrochloride(444057-64-1)
• EPA Substance Registry System: 3,3'-[Dithiobis[(2S,4S)-4,2-pyrrolidinediylcarbonyliMino]]bisbenzoic Acid Dihydrochloride(444057-64-1)

Safety Data

• Hazardous Substances Data: 444057-64-1(Hazardous Substances Data)

Usage

Description

3,3'-[Dithiobis[(2S,4S)-4,2-pyrrolidinediylcarbonyliMino]]bisbenzoic Acid Dihydrochloride is a complex organic compound with a unique structure that features a disulfide bond connecting two benzoic acid moieties, each attached to a pyrrolidine-based side chain. 3,3'-[Dithiobis[(2S,4S)-4,2-pyrrolidinediylcarbonyliMino]]bisbenzoic Acid Dihydrochloride is characterized by its chiral centers at the 2S and 4S positions, which contribute to its specific stereochemistry and potential biological activity.

Uses

Used in Pharmaceutical Industry:
3,3'-[Dithiobis[(2S,4S)-4,2-pyrrolidinediylcarbonyliMino]]bisbenzoic Acid Dihydrochloride is used as an impurity in the synthesis of Ertapenem (E635000), a broad-spectrum antibiotic. Its presence as an impurity is significant in the pharmaceutical industry because it can affect the purity and efficacy of the final drug product. Ensuring the control and removal of this impurity during the manufacturing process is crucial for maintaining the quality and safety of Ertapenem.

Upstream product

• 266337-24-0 C₂₄H₃₃NO₉P₂S 
• 266337-23-9 (2S-trans)-1-[bis(1-methylethoxy)phosphinyl]tetrahydro-4-hydroxy-2H-pyrrole-2-carboxylic acid diphenylphosphinyl ester 
• 220031-86-7 3-{[(2S,4S)-1-(Diisopropoxy-phosphoryl)-4-mercapto-pyrrolidine-2-carbonyl]-amino}-benzoic acid 
• 220030-10-4 (1S)-(3-oxo-2-thio-5-azabicyclo[2.2.1]hept-5-yl)phosphonic acid bis(1-methylethyl) ester 
• 99-05-8 meta-aminobenzoic acid 
• 117286-92-7 N‐(O,O‐diisopropylphosphoryl)-trans-4‐hydroxy-L-proline 
• 219909-83-8 (2S-cis)-3-[[(4-mercapto-2-pyrrolidinyl)carbonyl]amino]benzoic acid monohydrochloride 

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.