(S)-2-amino-N-((S)-1-(2-cyanoethoxy)-3-phenylpropan-2-yl)-3-methylbutanamide

Base Information

• Chemical Name: (S)-2-amino-N-((S)-1-(2-cyanoethoxy)-3-phenylpropan-2-yl)-3-methylbutanamide
• CAS No.: 1606176-85-5
• Molecular Formula: C₁₇H₂₅N₃O₂
• Molecular Weight: 303.404

Synonyms:(S)-2-amino-N-((S)-1-(2-cyanoethoxy)-3-phenylpropan-2-yl)-3-methylbutanamide

Chemical Property of (S)-2-amino-N-((S)-1-(2-cyanoethoxy)-3-phenylpropan-2-yl)-3-methylbutanamide

Chemical Property:

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Technology Process of (S)-2-amino-N-((S)-1-(2-cyanoethoxy)-3-phenylpropan-2-yl)-3-methylbutanamide

There total 4 articles about (S)-2-amino-N-((S)-1-(2-cyanoethoxy)-3-phenylpropan-2-yl)-3-methylbutanamide 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: 72.0%

acrylonitrile (107-13-1,25014-41-9) + (S)-2-amino-N-((S)-1-hydroxy-3-phenylpropan-2-yl)-3-methylbutanamide (158009-90-6) → (S)-2-amino-N-((S)-1-(2-cyanoethoxy)-3-phenylpropan-2-yl)-3-methylbutanamide (1606176-85-5) + (S)-2-((2-cyanoethyl)amino)-N-((S)-1-hydroxy-3-phenylpropan-2-yl)-3-methylbutanamide (1606176-86-6)

Guidance literature:

With n-butyllithium; copper(I) 2-hydroxy-3-methylbenzoate; 1,2-bis-(diphenylphosphino)ethane; In hexane; N,N-dimethyl-formamide; at 4 - 20 ℃; for 14h; chemoselective reaction; Inert atmosphere;

DOI:10.1002/anie.201309755

Reference yield:

L-Phenylalaninol (3182-95-4) → (S)-2-amino-N-((S)-1-(2-cyanoethoxy)-3-phenylpropan-2-yl)-3-methylbutanamide (1606176-85-5) + (S)-2-((2-cyanoethyl)amino)-N-((S)-1-hydroxy-3-phenylpropan-2-yl)-3-methylbutanamide (1606176-86-6)

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 / 14 h / 4 - 20 °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

Reference yield:

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) → (S)-2-amino-N-((S)-1-(2-cyanoethoxy)-3-phenylpropan-2-yl)-3-methylbutanamide (1606176-85-5) + (S)-2-((2-cyanoethyl)amino)-N-((S)-1-hydroxy-3-phenylpropan-2-yl)-3-methylbutanamide (1606176-86-6)

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 / 14 h / 4 - 20 °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

upstream raw materials:

acrylonitrile

(S)-2-amino-N-((S)-1-hydroxy-3-phenylpropan-2-yl)-3-methylbutanamide

L-Phenylalaninol

(S)-N-(benzyloxycarbonyl)valine

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