N-(1-(s)-Ethoxycarbonyl-3-Phenylpropyl)-L-Alanyl-Proline-Benzylester

Base Information

• Chemical Name: N-(1-(s)-Ethoxycarbonyl-3-Phenylpropyl)-L-Alanyl-Proline-Benzylester
• CAS No.: 120924-94-9
• Molecular Formula: C27H34N2O5
• Molecular Weight: 466.577
• DSSTox Substance ID: DTXSID001134856
• Mol file: 120924-94-9.mol

Synonyms:SCHEMBL10802722;MZFVAAUZTGRTKL-OYDLWJJNSA-N;DTXSID001134856;N-(1-(s)-Ethoxycarbonyl-3-Phenylpropyl)-L-Alanyl-Proline-Benzylester;120924-94-9;N-[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl-L-proline phenylmethyl ester

Chemical Property of N-(1-(s)-Ethoxycarbonyl-3-Phenylpropyl)-L-Alanyl-Proline-Benzylester

Chemical Property:

• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 466.24677219
• Heavy Atom Count: 34
• Complexity: 657

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2CCCC2C(=O)OCC3=CC=CC=C3
• Isomeric SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CCC[C@H]2C(=O)OCC3=CC=CC=C3

Technology Process of N-(1-(s)-Ethoxycarbonyl-3-Phenylpropyl)-L-Alanyl-Proline-Benzylester

There total 2 articles about N-(1-(s)-Ethoxycarbonyl-3-Phenylpropyl)-L-Alanyl-Proline-Benzylester 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: 76.0%

ethyl 2-amino-4-phenyl-(2S)-butyrate (46460-23-5) + N-<(2R)-2-(4-Toluenesulfonyloxy)propionyl>-L-proline Benzylester (136622-17-8) → N-<(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl>-L-alanyl-L-proline Benzylester (120924-94-9)

Guidance literature:

With triethylamine; In dimethyl sulfoxide; at 75 ℃; for 8h;

DOI:10.1248/cpb.39.1374

Reference yield:

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride (16652-71-4) + N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine hydrochloride (80828-26-8) → N-<(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl>-L-alanyl-L-proline Benzylester (120924-94-9)

Guidance literature:

N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine hydrochloride; With (chloromethylene)dimethyliminium chloride; In dichloromethane; at -10 - -5 ℃; for 0.666667h; Inert atmosphere;

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride; With potassium hydrogencarbonate; In dichloromethane; water; Inert atmosphere;

Reference yield:

N-<(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl>-L-alanyl-L-proline Benzylester (120924-94-9) → enalapril (75847-73-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 2h; under 735.5 Torr; Yield given; Ambient temperature;

DOI:10.1248/cpb.39.1374

upstream raw materials:

ethyl 2-amino-4-phenyl-(2S)-butyrate

N-<(2R)-2-(4-Toluenesulfonyloxy)propionyl>-L-proline Benzylester

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride

N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine hydrochloride

Downstream raw materials:

enalapril

Amprace

Refernces

• 1、 Kubota,Nunami,Yamagishi,Nishimoto,Hayashi. "Studies on angiotensin converting enzyme inhibitors. V. The diastereoselective synthesis of 2-oxoimidazolidine derivatives". . p. 1374 - 1377. Retrieved 2007/10/02.