[(S)-1-((3R,S),(4R,S)-1-acetyl-4-hydroxypyrrolidin-3-ylcarbamoyl)-3-methylbutyl]carbamic acid benzyl ester

Base Information

• Chemical Name: [(S)-1-((3R,S),(4R,S)-1-acetyl-4-hydroxypyrrolidin-3-ylcarbamoyl)-3-methylbutyl]carbamic acid benzyl ester
• CAS No.: 330975-16-1
• Molecular Formula: C₂₀H₂₉N₃O₅
• Molecular Weight: 391.467

Synonyms:[(S)-1-((3R,S),(4R,S)-1-acetyl-4-hydroxypyrrolidin-3-ylcarbamoyl)-3-methylbutyl]carbamic acid benzyl ester

Chemical Property of [(S)-1-((3R,S),(4R,S)-1-acetyl-4-hydroxypyrrolidin-3-ylcarbamoyl)-3-methylbutyl]carbamic acid benzyl ester

Chemical Property:

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Technology Process of [(S)-1-((3R,S),(4R,S)-1-acetyl-4-hydroxypyrrolidin-3-ylcarbamoyl)-3-methylbutyl]carbamic acid benzyl ester

There total 3 articles about [(S)-1-((3R,S),(4R,S)-1-acetyl-4-hydroxypyrrolidin-3-ylcarbamoyl)-3-methylbutyl]carbamic acid benzyl 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: 57.0%

acetic acid (64-19-7,77671-22-8) + [(S)-1-((3R,S),(4R,S)-4-hydroxypyrrolidin-3-ylcarbamoyl)-3-methylbutyl]carbamic acid benzyl ester hydrochloride → [(S)-1-((3R,S),(4R,S)-1-acetyl-4-hydroxypyrrolidin-3-ylcarbamoyl)-3-methylbutyl]carbamic acid benzyl ester (330975-16-1)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane;

DOI:10.1021/jm000320t

Reference yield:

Z-Leu-OH (2018-66-8) → [(S)-1-((3R,S),(4R,S)-1-acetyl-4-hydroxypyrrolidin-3-ylcarbamoyl)-3-methylbutyl]carbamic acid benzyl ester (330975-16-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / HOBt; EDC / CH₂Cl₂

2: 94 percent / HCl / ethyl acetate

3: 57 percent / EDC; HOBt / CH₂Cl₂

With hydrogenchloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; ethyl acetate;

DOI:10.1021/jm000320t

Reference yield:

(3R,S)-((S)-2-benzyloxycarbonylamino-4-methylpentanoylamino)-(4R,S)-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester (190142-00-8) → [(S)-1-((3R,S),(4R,S)-1-acetyl-4-hydroxypyrrolidin-3-ylcarbamoyl)-3-methylbutyl]carbamic acid benzyl ester (330975-16-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / HCl / ethyl acetate

2: 57 percent / EDC; HOBt / CH₂Cl₂

With hydrogenchloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; ethyl acetate;

DOI:10.1021/jm000320t

upstream raw materials:

acetic acid

Z-Leu-OH

(3R,S)-((S)-2-benzyloxycarbonylamino-4-methylpentanoylamino)-(4R,S)-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester

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