(S)-tert-Butyl 1-((S)-2-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)pyrrolidine-2-carboxylate

Base Information

• Chemical Name: (S)-tert-Butyl 1-((S)-2-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)pyrrolidine-2-carboxylate
• CAS No.: 108428-39-3
• Molecular Formula: C24H36N2O5
• Molecular Weight: 432.56
• DSSTox Substance ID: DTXSID701127024
• Mol file: 108428-39-3.mol

Synonyms:108428-39-3;Tert-butyl (2S)-1-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]pyrrolidine-2-carboxylate;(S)-tert-Butyl 1-((S)-2-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)pyrrolidine-2-carboxylate;N-[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl-L-proline 1,1-dimethylethyl ester;Enalapril tert-Butyl Ester;SCHEMBL905844;DTXSID701127024

Chemical Property of (S)-tert-Butyl 1-((S)-2-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)pyrrolidine-2-carboxylate

Chemical Property:

• PSA: 84.94000
• LogP: 3.19050
• Storage Temp.: Refrigerator
• Solubility.: Chloroform
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 432.26242225
• Heavy Atom Count: 31
• Complexity: 610

Purity/Quality:

Enalapriltert-ButylEster ^*data from reagent suppliers

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)OC(C)(C)C
• Isomeric SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CCC[C@H]2C(=O)OC(C)(C)C
• Uses: Protected Enalapril (E555250), an antihypertensive and an angiotensin-converting enzyme (ACE) inhibitor.

Technology Process of (S)-tert-Butyl 1-((S)-2-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)pyrrolidine-2-carboxylate

There total 12 articles about (S)-tert-Butyl 1-((S)-2-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)pyrrolidine-2-carboxylate 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: 74.0%

(S)-alanyl-(S)-proline tert-butyl ester (29375-30-2) + (R)-ethyl 2-bromo-4-phenylbutyrate (121842-77-1) → N-<(R)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-alaninyl-L-proline tert-butylester (120292-59-3) + N--L-alanyl>-L-proline tert butyl ester (108428-39-3)

Guidance literature:

With ammonium carbonate; In nitromethane; water; at 50 ℃; for 96h;

DOI:10.1248/cpb.37.280

Reference yield: 67.0%

proline tert-butyl ester (2812-46-6) + N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine hydrochloride (80828-26-8) → N--L-alanyl>-L-proline tert butyl ester (108428-39-3)

Guidance literature:

With diethyl cyanophosphonate; triethylamine; In N,N-dimethyl-formamide; for 1h;

DOI:10.1248/cpb.34.2852

Reference yield:

2-oxo-4-phenylbutanoic acid ethyl ester (64920-29-2) → N--L-alanyl>-L-proline tert butyl ester (108428-39-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 29 percent / H₂, AcONa, AcOH, molecular sieves 3A / Raney Ni / ethanol

2: 93 percent / HCl / H₂O / 4 h

3: 67 percent / diethyl phosphorocyanidate, Et₃N / dimethylformamide / 1 h

With hydrogenchloride; diethyl cyanophosphonate; 3 A molecular sieve; hydrogen; sodium acetate; acetic acid; triethylamine; nickel; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1248/cpb.34.2852

upstream raw materials:

Diazoethan

2-oxo-4-phenylbutyric acid

(S)-alanyl-(S)-proline tert-butyl ester

(R)-ethyl 2-bromo-4-phenylbutyrate

Downstream raw materials:

Amprace

enalapril

enalaprilate

Refernces

• 1、 Iwasaki,Kimura,Numao,Kondo. "A practical and diastereoselective synthesis of angiotensin converting enzyme inhibitors". . p. 280 - 283. Retrieved 2007/10/02.
• 2、 Miyake,Itoh,Oka. "Design and synthesis of N-[N-[(S)-1-ethoxycarbonyl-3-phenylpropyl]-L-alanyl]-N-(indan-2-y l)glycine (CV-3317), a new, potent angiotensin converting enzyme inhibitor". . p. 2852 - 2858. Retrieved 2007/10/02.