Benzamide → Ethyl 2-benzoylamino-3-oxobutanoate

HRID 453289Notes

Reaction equation

HRID 453289 reaction equation
[N+:1](=[C:3]([C:9](=[O:11])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N-].[C:12](N)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCCl.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Rh+3].[Rh+3]>[C:12]([NH:1][CH:3]([C:9](=[O:11])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 2331BenzamideHCID 538206Ethyl diazoacetoacetate

Product 1

HCID 11425196Ethyl 2-benzoylamino-3-oxobutanoateYield 75%

Reagents, catalysts & solvents 2

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

Procedure

A solution of ethyl 2-diazo-3-oxobutanoate (20 g, 128 mmol) in 1,2-dichloroethane (100 mL) was added over 16 h to a refluxing solution of benzamide (13 g, 107 mmol) and dirhodium tetraacetate (1.4 g, 3.2 mmol) in 1,2-dichloroethane (200 ml). The mixture was evaporated in vacuo and purified by flash chromatography to give ethyl 2-benzamido-3-oxobutanoate as a yellow oil (20 g, 50% yield).

Workup

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

Sources & evidence

ORD record
ord-f5e120d415b84caa8416be6b302b20f1
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

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