3-(Acetyl-methyl-amino)-2-diazo-3-oxo-propionic acid (S)-1-benzylcarbamoyl-2-methyl-propyl ester

Base Information

• Chemical Name: 3-(Acetyl-methyl-amino)-2-diazo-3-oxo-propionic acid (S)-1-benzylcarbamoyl-2-methyl-propyl ester
• CAS No.: 431069-47-5
• Molecular Formula: C₁₈H₂₂N₄O₅
• Molecular Weight: 374.396

Synonyms:3-(Acetyl-methyl-amino)-2-diazo-3-oxo-propionic acid (S)-1-benzylcarbamoyl-2-methyl-propyl ester

Chemical Property of 3-(Acetyl-methyl-amino)-2-diazo-3-oxo-propionic acid (S)-1-benzylcarbamoyl-2-methyl-propyl ester

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Technology Process of 3-(Acetyl-methyl-amino)-2-diazo-3-oxo-propionic acid (S)-1-benzylcarbamoyl-2-methyl-propyl ester

There total 2 articles about 3-(Acetyl-methyl-amino)-2-diazo-3-oxo-propionic acid (S)-1-benzylcarbamoyl-2-methyl-propyl 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: 78.0%

(S)-N-benzyl-2-hydroxy-3-methylbutanamide (179923-30-9) + 3-(acetyl-methyl-amino)-3-oxo-propionic acid (431069-31-7) → 3-(Acetyl-methyl-amino)-2-diazo-3-oxo-propionic acid (S)-1-benzylcarbamoyl-2-methyl-propyl ester (431069-47-5)

Guidance literature:

(S)-N-benzyl-2-hydroxy-3-methylbutanamide; 3-(acetyl-methyl-amino)-3-oxo-propionic acid; With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 5h;

With triethylamine; Methanesulfonyl azide; In diethyl ether; at 20 ℃; for 5h; Further stages.;

DOI:10.1021/ol017263y

Reference yield:

benzylamine (100-46-9) → 3-(Acetyl-methyl-amino)-2-diazo-3-oxo-propionic acid (S)-1-benzylcarbamoyl-2-methyl-propyl ester (431069-47-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 82 percent / HOBt; DCC / CH₂Cl₂ / 5 h / 20 °C

2.1: DMAP; DCC / CH₂Cl₂ / 5 h / 20 °C

2.2: 78 percent / MsN₃; Et₃N / diethyl ether / 5 h / 20 °C

With dmap; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1021/ol017263y

Reference yield: 88.0%

tert-butyl vinyl ether (926-02-3) + 3-(Acetyl-methyl-amino)-2-diazo-3-oxo-propionic acid (S)-1-benzylcarbamoyl-2-methyl-propyl ester (431069-47-5) → (S)-1-benzylcarbamoyl-2-methyl-propyl (1R,4S,5R)-5-(tert-butoxy)-1,2-dimethyl-3-oxo-7-oxa-2-aza-bicyclo[2.2.1]heptane-4-carboxylate + (1S,4R,5S)-5-tert-Butoxy-1,2-dimethyl-3-oxo-7-oxa-2-aza-bicyclo[2.2.1]heptane-4-carboxylic acid (S)-1-benzylcarbamoyl-2-methyl-propyl ester

Guidance literature:

With rhodium(II) perfluorobutyroamidate; In dichloromethane; at 23 ℃; for 8h;

DOI:10.1021/ol017263y

upstream raw materials:

(S)-N-benzyl-2-hydroxy-3-methylbutanamide

3-(acetyl-methyl-amino)-3-oxo-propionic acid

benzylamine

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