(S)-3-(4-allyloxy-3-chloro-phenyl)-2-amino-N-(1-cyano-cyclopropyl)-propionamide

Base Information

• Chemical Name: (S)-3-(4-allyloxy-3-chloro-phenyl)-2-amino-N-(1-cyano-cyclopropyl)-propionamide
• CAS No.: 1447710-53-3
• Molecular Formula: C₁₆H₁₈ClN₃O₂
• Molecular Weight: 319.791
• Mol file: 1447710-53-3.mol

Synonyms:(S)-3-(4-allyloxy-3-chloro-phenyl)-2-amino-N-(1-cyano-cyclopropyl)-propionamide

Chemical Property of (S)-3-(4-allyloxy-3-chloro-phenyl)-2-amino-N-(1-cyano-cyclopropyl)-propionamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-(4-allyloxy-3-chloro-phenyl)-2-amino-N-(1-cyano-cyclopropyl)-propionamide

There total 7 articles about (S)-3-(4-allyloxy-3-chloro-phenyl)-2-amino-N-(1-cyano-cyclopropyl)-propionamide 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: 100.0%

[(S)-2-(4-allyloxy-3-chloro-phenyl)-1-(1-cyano-cyclopropylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester (1447710-20-4) → (S)-3-(4-allyloxy-3-chloro-phenyl)-2-amino-N-(1-cyano-cyclopropyl)-propionamide (1447710-53-3)

Guidance literature:

With formic acid; at 23 ℃; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b01869

Reference yield: 96.0%

[(S)-2-(4-allyloxy-3-chloro-phenyl)-1-(1-cyano-cyclopropylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester → (S)-3-(4-allyloxy-3-chloro-phenyl)-2-amino-N-(1-cyano-cyclopropyl)-propionamide (1447710-53-3)

Guidance literature:

With formic acid; at 25 ℃; for 16h;

Reference yield:

(S)-3-(4-allyloxy-3-chloro-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester (1447710-21-5) → (S)-3-(4-allyloxy-3-chloro-phenyl)-2-amino-N-(1-cyano-cyclopropyl)-propionamide (1447710-53-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 2 h / 25 °C

1.2: pH 1

2.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 25 °C

3.1: formic acid / 16 h / 25 °C

With formic acid; lithium hydroxide monohydrate; water; N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; N,N-dimethyl-formamide;

upstream raw materials:

[(S)-2-(4-allyloxy-3-chloro-phenyl)-1-(1-cyano-cyclopropylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

(S)-3-(4-allyloxy-3-chloro-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester

methyl (S)-3-(3-chloro-4-hydroxyphenyl)-2-((tert-butoxycarbonyl)amino) propanoate

(S)-2-((tert-butoxycarbonyl)amino)-3-(3-chloro-4-hydroxyphenyl)propanoic acid (N-Boc-3-chlorotyrosine)