1-[(2S)-3-BroMo-2-Methyl-1-oxopropyl]-L-proline

Base Information

• Chemical Name: 1-[(2S)-3-BroMo-2-Methyl-1-oxopropyl]-L-proline
• CAS No.: 80629-35-2
• Molecular Formula: C9H14BrNO3
• Molecular Weight: 264.119
• Mol file: 80629-35-2.mol

Synonyms:1-[(2S)-3-Bromo-2-methyl-1-oxopropyl]-L-proline;Captopril EP Impurity B;

Chemical Property of 1-[(2S)-3-BroMo-2-Methyl-1-oxopropyl]-L-proline

Chemical Property:

• Melting Point: 110-114℃
• Boiling Point: 425.1±40.0 °C(Predicted)
• PKA: 3.52±0.20(Predicted)
• PSA: 57.61000
• Density: 1.555±0.06 g/cm3(Predicted)
• LogP: 1.03090

Purity/Quality:

98%,99%, ^*data from raw suppliers

Captopril impurity B European Pharmacopoeia (EP) Reference Standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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.

Technology Process of 1-[(2S)-3-BroMo-2-Methyl-1-oxopropyl]-L-proline

There total 1 articles about 1-[(2S)-3-BroMo-2-Methyl-1-oxopropyl]-L-proline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

3-bromo-2-methylpropanoyl chloride (71271-28-8) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → 1-(3-bromo-2S-methylpropionyl)-pyrrolidine-2S-carboxylic acid (80629-35-2,215780-02-2,80629-36-3)

Guidance literature:

With sodium hydroxide; 1.) 0 deg C, 1 h, 2.) room temperature, 3 h;

DOI:10.1002/jps.2600731251

Reference yield:

sodium ureido dithiocarbonate + sulfuric acid (7664-93-9) + 1-(3-bromo-2S-methylpropionyl)-pyrrolidine-2S-carboxylic acid (80629-35-2,215780-02-2,80629-36-3) + zinc (7440-66-6) → captopril (62571-86-2)

Guidance literature:

With hydrogenchloride; sodium bicarbonate; In hexane; ethyl acetate;

Reference yield:

1-(3-bromo-2S-methylpropionyl)-pyrrolidine-2S-carboxylic acid (80629-35-2,215780-02-2,80629-36-3) → captopril (62571-86-2)

Guidance literature:

With ammonium sulfide; In methanol; for 24h; Heating;

DOI:10.1002/jps.2600731251

upstream raw materials:

3-bromo-2-methylpropanoyl chloride

L-proline

Downstream raw materials:

captopril

Refernces