benzyl (S)-(1-((1-cyanocyclopropyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

Base Information

• Chemical Name: benzyl (S)-(1-((1-cyanocyclopropyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
• CAS No.: 191033-34-8
• Molecular Formula: C₂₁H₂₁N₃O₃
• Molecular Weight: 363.416
• Mol file: 191033-34-8.mol

Synonyms:benzyl (S)-(1-((1-cyanocyclopropyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

Chemical Property of benzyl (S)-(1-((1-cyanocyclopropyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (S)-(1-((1-cyanocyclopropyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

There total 5 articles about benzyl (S)-(1-((1-cyanocyclopropyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 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: 89.0%

N-Cbz-L-Phe (1161-13-3) + 1-amino-1-cyclopropanecarbonitrile hydrochloride (127946-77-4) → benzyl (S)-(1-((1-cyanocyclopropyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (191033-34-8)

Guidance literature:

N-Cbz-L-Phe; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; for 0.833333h;

1-amino-1-cyclopropanecarbonitrile hydrochloride; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 12h;

DOI:10.1016/j.bmcl.2017.10.002

Reference yield:

ethyleneglycol sulfate (1072-53-3) + N-Cbz-L-Phe (1161-13-3) → benzyl (S)-(1-((1-cyanocyclopropyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (191033-34-8)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 5h;

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → benzyl (S)-(1-((1-cyanocyclopropyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (191033-34-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / 4-methylmorpholine, dicyclohexylcarbodiimide, 1-hydroxybenzotriazole / CH₂Cl₂ / 18 h

2: 50 percent / n-BuLi, hexamethyl phosphoramide, LDA / tetrahydrofuran; hexane / 5 h / -78 °C

3: 2.) NaHCO₃ / 1.) THF/CH₂Cl₂

With 4-methyl-morpholine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; sodium hydrogencarbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

upstream raw materials:

ethyleneglycol sulfate

N-Cbz-L-Phe

benzyl chloroformate

(S)-tert-butyl (1-((1-cyanocyclopropyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

Downstream raw materials:

N-Cbz-(S)-phenylalanine-(S)-cyclopropanecarboxylic acid methyl ester