Bromoacetyl bromide → {2-[(2-Bromoacetyl)-(5-fluoro-2-methylphenyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl ester

HRID 1694942Notes

Reaction equation

HRID 1694942 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[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[CH3:23])([CH3:9])([CH3:8])[CH3:7].C(=O)(O)[O-].[Na+]>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[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[CH3:23])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 61147Bromoacetyl bromideHCID 516892Sodium BicarbonateHCID 66645553[1,1-Dimethyl-2-(5-fluoro-2-methylphenylamino)ethyl]carbamic acid t-butyl ester

Product 1

HCID 66645460{2-[(2-Bromoacetyl)-(5-fluoro-2-methylphenyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl esterYield 89.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1.67 ml of bromoacetyl bromide (19.1 mmol) was added to a solution of 5.68 g of [1,1-dimethyl-2-(5-fluoro-2-methylphenylamino)ethyl]carbamic acid t-butyl ester obtained in Example (70a) (19.1 mmol) in N,N-dimethylacetamide (95 ml) under ice-cooling, and the mixture was stirred at the same temperature for 10 minutes. A saturated sodium bicarbonate aqueous solution 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. Hexane was added to the residue, and the solid was collected by filtration to obtain 7.1 g of the title compound (yield: 89%).

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. additionHexane was added to the residue
  8. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-6604fb182c474c0b9060490cea280215
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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