80629-35-2

Basic information

• Product Name: 1-[(2S)-3-BroMo-2-Methyl-1-oxopropyl]-L-proline
• Synonyms: 1-[(2S)-3-BroMo-2-Methyl-1-oxopropyl]-L-proline;(2S)-1-[(2S)-3-Bromo-2-methylpropanoyl]pyrrolidine-2-carboxylic acid;Captopril impurity B;(S)-1-((S)-3-bromo-2-methylpropanoyl)pyrrolidine-2-carboxylic acid
• CAS NO: 80629-35-2
• Molecular Formula: C₉H₁₄BrNO₃
• Molecular Weight: 264.11636
• Product Categories: Inhibitors, Intermediates, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 80629-35-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 110-114℃
• Boiling Point: 425.1±40.0 °C(Predicted)
• Appearance: /
• Density: 1.555±0.06 g/cm3(Predicted)
• PKA: 3.52±0.20(Predicted)
• CAS DataBase Reference: 1-[(2S)-3-BroMo-2-Methyl-1-oxopropyl]-L-proline(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(2S)-3-BroMo-2-Methyl-1-oxopropyl]-L-proline(80629-35-2)
• EPA Substance Registry System: 1-[(2S)-3-BroMo-2-Methyl-1-oxopropyl]-L-proline(80629-35-2)

Safety Data

• Hazardous Substances Data: 80629-35-2(Hazardous Substances Data)

Usage

Uses

1-[(2S)-3-Bromo-2-methyl-1-oxopropyl]-L-proline is an intermediate in the synthetic preparation of Captopril (C175750), a orally active angiotensin-converting enzyme (ACE) inhibitor.

Upstream product

• 71271-28-8 3-bromo-2-methylpropanoyl chloride 
• 147-85-3 L-proline 

Downstream Products

• 62571-86-2 captopril 

Relevant articles and documents

An improved synthesis of captopril

An improved synthesis of captopril using methacrylic acid as the starting material is described. Treatment of methacrylic acid (I) with a hydrogen halide gave the 3-halogeno-2-methylpropanoic acids II and III, which were treated with thionyl chloride to yield the corresponding 3-halogeno-2-methylpropanoyl chlorides IV and V. Treatment of IV or V with L-proline yielded the N-(R,S-3-halogeno-2-methylpropanoyl)-L-prolines VI and VII, which were separated into optically pure R- and S-diastereoisomers using dicyclohexylamine. Treatment of halides of VI or VII with methanolic ammonium hydrosulfide gave captopril in 28% yield.