Water → 2-(2-Nitrobenzoylamino)-3-oxobutanoic acid ethyl ester

HRID 2061106Notes

Reaction equation

[N+](=[CH:3][C:4](=[O:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[N-].[N+:12]([C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([NH2:19])=[O:18])([O-:14])=[O:13].O.C(OCC)(=O)C>C(Cl)Cl>[CH2:9]([O:8][C:6](=[O:7])[CH:5]([NH:19][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=1[N+:12]([O-:14])=[O:13])[C:4](=[O:11])[CH3:3])[CH3:10]

Participants

Conditions

Temperature: 40 °C

Procedure

Rh2(OAc)4 (30 mg, 0.063 mmol) was added to a solution of ethyl diazoacetoacetate (1.0 g, 6.32 mmol) and 2-nitrobenzamide (1.05 g, 6.32 mmol) in methylene chloride (15 mL), and the mixture was stirred at 40° C. for a day and a night. Water was then added to the reaction mixture, extraction was performed with ethyl acetate, and the organic extract was washed with water and saturated saline. After drying over magnesium sulfate, it was concentrated under reduced pressure to yield a crude product, which was then purified by column chromatography to yield the title compound (1.42 g, 77%) as a yellow oil.

Workup

extractionthe organic extract
washwas washed with water and saturated saline
dry with materialAfter drying over magnesium sulfate, it
concentrationwas concentrated under reduced pressure
customto yield a crude product, which
customwas then purified by column chromatography

Sources & evidence

ORD record: ord-85368fe3c43446fcb9e656848d22b331
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278465B2

Reaction notes

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