N-[1-(S)-Benzyloxycarbonyl-3-phenylpropyl]-L-alanine tert-Butyl Ester

Base Information

• Chemical Name: N-[1-(S)-Benzyloxycarbonyl-3-phenylpropyl]-L-alanine tert-Butyl Ester
• CAS No.: 117560-14-2
• Molecular Formula: C24H31NO4
• Molecular Weight: 397.50724
• Mol file: 117560-14-2.mol

Synonyms:N-[1-(S)-Benzyloxycarbonyl-3-phenylpropyl]-L-alanine tert-Butyl Ester

Chemical Property of N-[1-(S)-Benzyloxycarbonyl-3-phenylpropyl]-L-alanine tert-Butyl Ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 502.176°C at 760 mmHg
• Flash Point: 257.507°C
• PSA: 64.63000
• Density: 1.09g/cm³
• LogP: 4.44190
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

97% ^*data from raw suppliers

N-[1-(S)-Benzyloxycarbonyl-3-phenylpropyl]-L-alaninetert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate in the preparation of Imidaprilat

Technology Process of N-[1-(S)-Benzyloxycarbonyl-3-phenylpropyl]-L-alanine tert-Butyl Ester

There total 9 articles about N-[1-(S)-Benzyloxycarbonyl-3-phenylpropyl]-L-alanine 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: 40.8%

tert-butyl 2-bromopropionate (39149-80-9,54631-38-8,98104-35-9,32821-07-1) + p-tolylsulfonic caid salt of L-homophenylalanine benzyl ester (117560-24-4) → N-<1(S)-(benzyloxycarbonyl)-3-phenylpropyl>-L-alanine tert-butyl ester (117560-14-2)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide; for 30h; Ambient temperature;

DOI:10.1021/jm00122a003

Reference yield: 23.0%

Ala-OtBu (21691-50-9) + 2-trifluoromethanesulfonyloxy-4-phenylbutyric acid benzyl ester (112076-94-5) → N-<1(R)-(benzyloxycarbonyl)-3-phenylpropyl>-L-alanine tert-butyl ester (130275-81-9) + N-<1(S)-(benzyloxycarbonyl)-3-phenylpropyl>-L-alanine tert-butyl ester (117560-14-2)

Guidance literature:

With triethylamine; In dichloromethane; 1.) RT, 16 h, 2.) reflux, 1 h;

DOI:10.1021/jm00105a066

Reference yield:

2-bromo-4-phenyl butanoic acid (16503-46-1) → N-<1(S)-(benzyloxycarbonyl)-3-phenylpropyl>-L-alanine tert-butyl ester (117560-14-2)

Guidance literature:

Multi-step reaction with 5 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

5: 40.8 percent / K₂CO₃ / dimethylsulfoxide / 30 h / Ambient temperature

With ammonium hydroxide; potassium carbonate; In water; dimethyl sulfoxide; benzene;

DOI:10.1021/jm00122a003

upstream raw materials:

tert-butyl 2-bromopropionate

p-tolylsulfonic caid salt of L-homophenylalanine benzyl ester

Ala-OtBu

2-trifluoromethanesulfonyloxy-4-phenylbutyric acid benzyl ester

Downstream raw materials:

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

(R)-3-[(S)-2-((S)-1-Benzyloxycarbonyl-3-phenyl-propylamino)-propionyl]-5-tert-butyl-2,3-dihydro-[1,3,4]thiadiazole-2-carboxylic acid benzyl ester

Utibaprilat

(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