Benzamide → Tert-butyl 2-benzamido-3-oxobutanoate

HRID 1799098Notes

Reaction equation

HRID 1799098 reaction equation
[N+:1](=[C:3]([C:11](=[O:13])[CH3:12])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[N-].[C:14](N)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClCCCl.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Rh+3].[Rh+3]>[C:14]([NH:1][CH:3]([C:11](=[O:13])[CH3:12])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 2331BenzamideHCID 538143121-tert-Butoxy-2-diazonio-3-oxobut-1-en-1-olate

Product 1

HCID 58551885Tert-butyl 2-benzamido-3-oxobutanoateYield 51%

Reagents, catalysts & solvents 2

HCID 86657289Di-rhodium tetraacetateCatalystHCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of tert-butyl 2-diazo-3-oxobutanoate (13.1 g, 71.7 mmol) in 1,2-dichloroethane was added over 12 h to a refluxing solution of benzamide (6.16 g, 50.8 mmol) and dirhodium tetraacetate (786 mg, 1.78 mmol) in 1,2-dichloroethane (75 ml). The mixture was evaporated in vacuo and purified by flash chromatography to give tert-butyl 2-benzamido-3-oxobutanoate as a white solid (6.97 g, 51% yield).

Workup

  1. customThe mixture was evaporated in vacuo
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-38ac381445164a40875b9ac8f0ab3b96
Source dataset
uspto-grants-2013_01
Patent number
US08343997B2

Reaction notes

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