(S)-tert-butyl 2-((S)-2-((2-cyanoethyl)amino)-3-hydroxypropanamido)-3-phenylpropanoate

Base Information

Chemical Name:(S)-tert-butyl 2-((S)-2-((2-cyanoethyl)amino)-3-hydroxypropanamido)-3-phenylpropanoate
CAS No.:1606176-88-8
Molecular Formula:C₁₉H₂₇N₃O₄
Molecular Weight:361.441
Hs Code.:

Synonyms:(S)-tert-butyl 2-((S)-2-((2-cyanoethyl)amino)-3-hydroxypropanamido)-3-phenylpropanoate

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Chemical Property of (S)-tert-butyl 2-((S)-2-((2-cyanoethyl)amino)-3-hydroxypropanamido)-3-phenylpropanoate

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Technology Process of (S)-tert-butyl 2-((S)-2-((2-cyanoethyl)amino)-3-hydroxypropanamido)-3-phenylpropanoate

There total 2 articles about (S)-tert-butyl 2-((S)-2-((2-cyanoethyl)amino)-3-hydroxypropanamido)-3-phenylpropanoate 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: 58.0%

: 79432-20-5
H-Ser-Phe-OBu^t

: 107-13-1,25014-41-9
acrylonitrile

: 1606176-87-7
(S)-tert-butyl 2-((S)-2-amino-3-(2-cyanoethoxy)propanamido)-3-phenylpropanoate

: 1606176-88-8
(S)-tert-butyl 2-((S)-2-((2-cyanoethyl)amino)-3-hydroxypropanamido)-3-phenylpropanoate

Guidance literature:: With n-butyllithium; copper(I) 2-hydroxy-3-methylbenzoate; 1,2-bis-(diphenylphosphino)ethane; In hexane; N,N-dimethyl-formamide; at 4 ℃; for 6h; chemoselective reaction; Inert atmosphere;
DOI:10.1002/anie.201309755

Reference yield:

: 16874-17-2
L-phenylalanine tert-butyl ester

: 1606176-87-7
(S)-tert-butyl 2-((S)-2-amino-3-(2-cyanoethoxy)propanamido)-3-phenylpropanoate

: 1606176-88-8
(S)-tert-butyl 2-((S)-2-((2-cyanoethyl)amino)-3-hydroxypropanamido)-3-phenylpropanoate

Guidance literature:: Multi-step reaction with 3 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / N,N-dimethyl-formamide / 25 h / 0 - 20 °C / Inert atmosphere

2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 20 °C / Inert atmosphere

3: 1,2-bis-(diphenylphosphino)ethane; n-butyllithium; copper(I) 2-hydroxy-3-methylbenzoate / N,N-dimethyl-formamide; hexane / 6 h / 4 °C / Inert atmosphere

With 4-methyl-morpholine; n-butyllithium; copper(I) 2-hydroxy-3-methylbenzoate; palladium 10% on activated carbon; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1,2-bis-(diphenylphosphino)ethane; In methanol; hexane; N,N-dimethyl-formamide; 3: |Michael Addition;
DOI:10.1002/anie.201309755