Enalapril tert-Butyl Ester

Base Information

• Chemical Name: Enalapril tert-Butyl Ester
• CAS No.: 108428-39-3
• Molecular Formula: C24H36N2O5
• Molecular Weight: 432.56
• Mol file: 108428-39-3.mol

Synonyms:.N-[N-((S)-1-ethoxycarbonyl-3-phenylpropyl)-L-alanyl]-L-proline tert butyl ester;Enalapril tert-Butyl Ester;N-[(S)-1-(ethoxycarbonyl)-3-phenylpropyl]-L-alanyl-L-proline tert-butylester;

Chemical Property of Enalapril tert-Butyl Ester

Chemical Property:

• PSA: 84.94000
• LogP: 3.19050
• Storage Temp.: Refrigerator
• Solubility.: Chloroform

Purity/Quality:

Enalapriltert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Protected Enalapril (E555250), an antihypertensive and an angiotensin-converting enzyme (ACE) inhibitor.

Technology Process of Enalapril tert-Butyl Ester

There total 12 articles about Enalapril tert-Butyl Ester 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.