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

HRID 1046777Notes

Reaction equation

HRID 1046777 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

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 118762-NitrobenzamideHCID 539990751-Diazonio-4-ethoxy-4-oxobut-1-en-2-olate

Product 1

HCID 591394022-(2-Nitrobenzoylamino)-3-oxobutanoic acid ethyl esterYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

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

Sources & evidence

ORD record
ord-bbb75d63f6654aa48b5e6f1d70980744
Source dataset
uspto-grants-2013_10
Patent number
US08569378B2

Reaction notes

Loading…