(2S)-1-[(2S)-3-Bromo-2-methylpropanoyl]pyrrolidine-2-carboxylic Acid

Base Information

• Chemical Name: (2S)-1-[(2S)-3-Bromo-2-methylpropanoyl]pyrrolidine-2-carboxylic Acid
• CAS No.: 80629-35-2
• Molecular Formula: C9H14BrNO3
• Molecular Weight: 264.119
• UNII: 6HCR5N6952
• DSSTox Substance ID: DTXSID20230443
• Wikidata: Q27264917
• Mol file: 80629-35-2.mol

Synonyms:80629-35-2;Captopril EP Impurity B;Captopril Impurity B;(2S)-1-[(2S)-3-Bromo-2-methylpropanoyl]pyrrolidine-2-carboxylic Acid;(S)-1-((S)-3-Bromo-2-methylpropanoyl)pyrrolidine-2-carboxylic acid;6HCR5N6952;L-Proline, 1-((2S)-3-bromo-2-methyl-1-oxopropyl)-;L-Proline, 1-(3-bromo-2-methyl-1-oxopropyl)-, (S)-;(2S)-1-((2S)-3-Bromo-2-methylpropanoyl)pyrrolidine-2-carboxylic acid;1-[(2S)-3-BroMo-2-Methyl-1-oxopropyl]-L-proline;Captopril impurity B [EP];UNII-6HCR5N6952;Captopril specified impurity B [EP];SCHEMBL10802283;DTXSID20230443;CAPTOPRIL IMPURITY B [EP IMPURITY];HY-137768;CS-0141854;A864674;Q27264917;(S)-1-((S)-3-Bromo-2-methylpropanoyl)pyrrolidine-2-carboxylicacid;Captopril Imp. B (EP)

Chemical Property of (2S)-1-[(2S)-3-Bromo-2-methylpropanoyl]pyrrolidine-2-carboxylic Acid

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
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 263.01571
• Heavy Atom Count: 14
• Complexity: 244

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:

• Canonical SMILES: CC(CBr)C(=O)N1CCCC1C(=O)O
• Isomeric SMILES: C[C@H](CBr)C(=O)N1CCC[C@H]1C(=O)O
• 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 (2S)-1-[(2S)-3-Bromo-2-methylpropanoyl]pyrrolidine-2-carboxylic Acid

There total 1 articles about (2S)-1-[(2S)-3-Bromo-2-methylpropanoyl]pyrrolidine-2-carboxylic Acid 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