Water → {2-[(2-Bromoacetyl)-(2,6-difluorophenyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl ester

HRID 1694926Notes

Reaction equation

HRID 1694926 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[C:6]([O:10][C:11](=[O:26])[NH:12][C:13]([CH3:25])([CH3:24])[CH2:14][NH:15][C:16]1[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=1[F:23])([CH3:9])([CH3:8])[CH3:7].O>CN(C)C(=O)C>[C:6]([O:10][C:11](=[O:26])[NH:12][C:13]([CH3:25])([CH3:24])[CH2:14][N:15]([C:3](=[O:4])[CH2:2][Br:1])[C:16]1[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=1[F:23])([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 61147Bromoacetyl bromideHCID 66645887[2-(2,6-Difluorophenylamino)-1,1-dimethylethyl]carbamic acid t-butyl ester

Product 1

HCID 66645630{2-[(2-Bromoacetyl)-(2,6-difluorophenyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1.17 ml of bromoacetyl bromide (13.4 mmol) was added to a solution of 3.66 g of [2-(2,6-difluorophenylamino)-1,1-dimethylethyl]carbamic acid t-butyl ester obtained in Example (60a) (12.2 mmol) in N,N-dimethylacetamide (61 ml) under ice-cooling, and the mixture was stirred at the same temperature for five minutes. Water was added to the reaction mixture, followed by extraction with diethyl ether. Then, the organic layer was washed with brine and dried over anhydrous sodium 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) to obtain 5.14 g of the title compound (yield: quant.).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with diethyl ether
  3. washThen, the organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium 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)

Sources & evidence

ORD record
ord-c6c76cd528144d14b73a18801d7756fc
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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