Isobutyrylproline

Base Information

• Chemical Name: Isobutyrylproline
• CAS No.: 23500-15-4
• Molecular Formula: C9H15NO3
• Molecular Weight: 185.22000
• European Community (EC) Number: 641-711-1
• UNII: 27JC6R80S1
• DSSTox Substance ID: DTXSID10178067
• Nikkaji Number: J1.160.065D
• Wikidata: Q27254207
• Mol file: 23500-15-4.mol

Synonyms:23500-15-4;isobutyrylproline;Captopril EP Impurity E;(2S)-1-(2-methylpropanoyl)pyrrolidine-2-carboxylic acid;L-Proline, 1-(2-methyl-1-oxopropyl)-;(S)-1-Isobutyrylpyrrolidine-2-carboxylic acid;Proline, 1-isobutyryl-, L;1-Isobutyrylproline, (-)-;27JC6R80S1;(2S)-1-[2-Methylpropanoyl]-pyrrolidine-2-carboxylic Acid;Captopril Impurity E;Captopril impurity E [EP];UNII-27JC6R80S1;MFCD12795270;N-isobutyrylproline;Captopril Imp. E (EP);Captopril specified impurity E [EP];N-dimethylacetyl (l)-proline;SCHEMBL3045658;DTXSID10178067;WKQUFVTUGGLNNO-ZETCQYMHSA-N;AKOS010372311;AKOS015837583;CAPTOPRIL IMPURITY E [EP IMPURITY];HY-137772;CS-0141869;F21102;Q27254207

Chemical Property of Isobutyrylproline

Chemical Property:

• Melting Point: 122.6-123.7℃
• Boiling Point: 369.6±35.0 °C(Predicted)
• PKA: 3.71±0.20(Predicted)
• PSA: 57.61000
• Density: 1.182±0.06 g/cm3(Predicted)
• LogP: 0.65590
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 185.10519334
• Heavy Atom Count: 13
• Complexity: 225

Purity/Quality:

> 95% ^*data from raw suppliers

(2S)?-?1-?(2-?Methylpropanoyl)?pyrrolidine-?2-?carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(=O)N1CCCC1C(=O)O
• Isomeric SMILES: CC(C)C(=O)N1CCC[C@H]1C(=O)O
• Uses: (2S)?-?1-?(2-?methylpropanoyl)?pyrrolidine-?2-?carboxylic Acid (Captopril EP Impurity E) is an impurity of Captopril (C175750), an orally active angiotensin-converting enzyme (ACE) inhibitor(1) which acts as a neuroprotective & neuroresearch product.

Technology Process of Isobutyrylproline

There total 4 articles about Isobutyrylproline 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: 96.0%

(S)-methyl 1-(isobutyryl)pyrrolidine-2-carboxylate (177747-23-8) → 1-(1-oxo-2-methylpropyl)-L-proline (23500-15-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃;

DOI:10.1002/hlca.200690178

Reference yield: 83.0%

captopril (62571-86-2) → 1-(1-oxo-2-methylpropyl)-L-proline (23500-15-4)

Guidance literature:

With triethyl borane; tributylphosphine; triethyl phosphite; In acetonitrile; for 36h; Irradiation;

DOI:10.1016/S0957-4166(99)00265-7

Reference yield:

L-proline ethyl ester monohydrochloride (33305-75-8,131477-20-8) + isobutyric Acid (79-31-2) → 1-(1-oxo-2-methylpropyl)-L-proline (23500-15-4)

Guidance literature:

L-proline ethyl ester monohydrochloride; isobutyric Acid; With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane;

With sodium hydroxide; In methanol;

DOI:10.3987/COM-05-S(T)73

upstream raw materials:

captopril

L-proline ethyl ester monohydrochloride

isobutyric Acid

(S)-methyl 1-(isobutyryl)pyrrolidine-2-carboxylate

Downstream raw materials:

2-oxo-2-phenylethyl N-{2-[((S)-2-{[(benzyloxy)carbonyl]amino}-3-phenyl-1-oxopropyl)amino]-2-methyl-1-oxopropyl}-L-prolinate

prop-2-enyl N-{2-[((2S,3S)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-1-oxopentyl)amino]-2-methyl-1-oxopropyl}-L-prolinate

2-oxo-2-phenylethyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate

2-oxo-2-phenylethyl N-(2-methyl-1-thioxopropyl)-L-prolinate

Refernces

• 1、 Ishige, Hirohide,Ishiyama, Nobuo,Mimura, Mitsuo,Hayashida, Mitsuo,Okuno, Tadashi,Ukai, Kiyoharu,Kiyofuji, Takeshi,Yoneda, Yasuo,Tauchi, Shinji,Aoyama, Akinori,Inoguchi, Kiyoshi. "Novel series of highly potent non-peptide growth hormone secretagogues with improved bioavailability". . p. 561 - 566. Retrieved 2007/10/03.
• 2、 Cuesta, Javier,Arsequell, Gemma,Valencia, Gregorio,Gonzalez, Asensio. "Photochemical desulfurization of thiols and disulfides". . p. 2643 - 2646. Retrieved 2007/10/03.