Water → HCID 66645676, compound

HRID 1694914Notes

Reaction equation

HRID 1694914 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]([O:11][C:12](=[O:29])[NH:13][C:14]([CH3:28])([CH3:27])[CH2:15][N:16]([C:23](=[O:26])[CH2:24]Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:10])([CH3:9])[CH3:8].O>CN(C)C=O>[C:7]([O:11][C:12]([N:13]1[CH2:24][C:23](=[O:26])[N:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][C:14]1([CH3:28])[CH3:27])=[O:29])([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 10796Cesium carbonateHCID 66645513HCID 66645513, compound

Product 1

HCID 66645676HCID 66645676, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

11.19 g of cesium carbonate (34.4 mmol) was added to a solution of 4.41 g of {2-[(2-bromoacetyl)phenylamino]-1,1-dimethylethyl}carbamic acid t-butyl ester obtained in the above reaction (11.5 mmol) in N,N-dimethylformamide (58 ml) under ice-cooling, and the mixture was stirred at room temperature for 18 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:hexane/ethyl acetate=10/1-5/1-2/1) to obtain 1.83 g of 2,2-dimethyl-5-oxo-4-phenylpiperazine-1-carboxylic acid t-butyl ester (yield: 53%).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThen, the organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (elution solvent:hexane/ethyl acetate=10/1-5/1-2/1)

Sources & evidence

ORD record
ord-a78b112aaf264572b73911a0c78ede0d
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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