(2S)-2-Amino-benzenebutanoic Acid Benzyl Ester, Tosylate Salt

Base Information

• Chemical Name: (2S)-2-Amino-benzenebutanoic Acid Benzyl Ester, Tosylate Salt
• CAS No.: 117560-24-4
• Molecular Formula: C24H27NO5S
• Molecular Weight: 441.53988
• Mol file: 117560-24-4.mol

Synonyms:(2S)-2-Amino-benzenebutanoic Acid Benzyl Ester, Tosylate Salt;(αS)-α-AMino-benzenebutanoic Acid PhenylMethyl Ester 4-Methylbenzenesulfonate

Chemical Property of (2S)-2-Amino-benzenebutanoic Acid Benzyl Ester, Tosylate Salt

Chemical Property:

• PSA: 115.07000
• LogP: 5.71270
• Storage Temp.: Refrigerator
• Solubility.: DMSO, Methanol

Purity/Quality:

98%Min ^*data from raw suppliers

(2S)-2-Amino-benzenebutanoicAcidBenzylEsterTosylateSalt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An intermediate in the preparation of Imidaprilat

Technology Process of (2S)-2-Amino-benzenebutanoic Acid Benzyl Ester, Tosylate Salt

There total 8 articles about (2S)-2-Amino-benzenebutanoic Acid Benzyl Ester, Tosylate Salt 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: 90.0%

D-homophenylalanine (82795-51-5) + toluene-4-sulfonic acid (104-15-4) + benzyl alcohol (100-51-6,185532-71-2) → p-tolylsulfonic caid salt of D-homophenylalanine benzyl ester (117560-24-4)

Guidance literature:

In toluene; for 4h; Heating;

DOI:10.1248/cpb.40.1619

Reference yield: 79.0%

D-homophenylalanine (943-73-7) + toluene-4-sulfonic acid (104-15-4) + benzyl alcohol (100-51-6,185532-71-2) → p-tolylsulfonic caid salt of L-homophenylalanine benzyl ester (117560-24-4)

Guidance literature:

In toluene; for 4h; Heating;

DOI:10.1248/cpb.40.1619

Reference yield:

2-bromo-4-phenyl butanoic acid (16503-46-1) → p-tolylsulfonic caid salt of L-homophenylalanine benzyl ester (117560-24-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 28percent aq. NH₃ / 168 h / Ambient temperature

3: CoCl₂ / H₂O / 72 h / 37 °C / aminoacylase (from Aspergillus oryzae); pH 7

4: benzene / 6 h / Heating

With ammonium hydroxide; In water; benzene;

DOI:10.1021/jm00122a003

upstream raw materials:

D-homophenylalanine

toluene-4-sulfonic acid

benzyl alcohol

2-(acetylamino)-4-phenylbutanoic acid

Downstream raw materials:

{2S-[2α,3β(S)]}-Oxirane carboxylic acid 3-[({3-Phenyl-1-[(benzyloxy)carbonyl]propyl}amino)carbonyl] ethyl ester

(S)-3-[(S)-2-((S)-1-Benzyloxycarbonyl-3-phenyl-propylamino)-propionyl]-2-oxo-imidazolidine-1,4-dicarboxylic acid 1-benzyl ester 4-tert-butyl ester

(S)-3-[(S)-2-((S)-1-Benzyloxycarbonyl-3-phenyl-propylamino)-propionyl]-2-oxo-imidazolidine-1,4-dicarboxylic acid 1-benzyl ester 4-tert-butyl ester; compound with (Z)-but-2-enedioic acid

(S)-2-((S)-1-tert-Butoxycarbonyl-ethylamino)-4-phenyl-butyric acid benzyl ester; compound with (Z)-but-2-enedioic acid

Refernces

• 1、 Kubota,Nunami,Hayashi,Hashimoto,Ogiku,Matsuoka,Ishida. "Studies on angiotensin converting enzyme inhibitors. VI. Synthesis and angiotensin converting enzyme inhibitory activities of the dicarboxylic acid derivative of imidapril and its diastereoisomers". . p. 1619 - 1622. Retrieved 2007/10/02.