Phenacyl bromide → Diethyl acetamido(2-oxo-2-phenylethyl)propanedioate

HRID 853812Notes

Reaction equation

HRID 853812 reaction equation
[H-].[Na+].[O-]CC.[Na+].[CH2:7]([O:9][C:10](=[O:21])[CH:11]([NH:17][C:18](=[O:20])[CH3:19])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:8].Br[CH2:23][C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:25]>C(O)C>[CH2:15]([O:14][C:12](=[O:13])[C:11]([NH:17][C:18](=[O:20])[CH3:19])([CH2:23][C:24](=[O:25])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:10]([O:9][CH2:7][CH3:8])=[O:21])[CH3:16]

Participants

6

Reactant 4

HCID 6259Phenacyl bromideHCID 14041Acetamidomalonic acid diethyl esterHCID 24758Sodium hydrideHCID 2723922Sodium ethoxide

Product 1

HCID 233989Diethyl acetamido(2-oxo-2-phenylethyl)propanedioate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium hydride (15 mmol) is added to anhydrous ethanol (50 mL) and to the resulting sodium ethoxide solution is added 2-acetylaminomalonic acid diethyl ester (15 mmol) in one portion. The resulting mixture is stirred at room temperature for 30 minutes. A solution of 2-bromoacetophenone (10 mmol) in ethanol (10 mL) is then added and the resulting mixture is stirred at room temperature for 12 hours. After concentrating under reduced pressure, the residue is dissolved in EtOAc and water. The organic phase is washed with brine and dried over Na2SO4. After removal of the solvent, the crude material is purified by column chromatography using EtOAc/hexane (1/3) giving 2-acetylamino-2-(2-oxo-2-phenyl-ethyl)-malonic acid diethyl ester as white solid; MS: (ES+): 336.1 (M+1)+.

Workup

  1. stirringthe resulting mixture is stirred at room temperature for 12 hours
  2. concentrationAfter concentrating under reduced pressure
  3. dissolutionthe residue is dissolved in EtOAc
  4. washThe organic phase is washed with brine
  5. dry with materialdried over Na2SO4
  6. customAfter removal of the solvent
  7. customthe crude material is purified by column chromatography

Sources & evidence

ORD record
ord-6fa26508b22e43b5aa871bebd335a2ba
Source dataset
uspto-grants-2007_08
Patent number
US07256206B2

Reaction notes

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