Ammonium Chloride → HCID 66645797, compound

HRID 1694939Notes

Reaction equation

HRID 1694939 reaction equation
CC(C)([O-])C.[K+].[C:7]([O:11][C:12](=[O:31])[NH:13][C:14]([CH3:30])([CH3:29])[CH2:15][N:16]([C:25](=[O:28])[CH2:26]Br)[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=1[CH3:24])([CH3:10])([CH3:9])[CH3:8].[Cl-].[NH4+]>O1CCCC1.O>[C:7]([O:11][C:12]([N:13]1[CH2:26][C:25](=[O:28])[N:16]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=2[CH3:24])[CH2:15][C:14]1([CH3:30])[CH3:29])=[O:31])([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 66645692HCID 66645692, compound

Product 1

HCID 66645797HCID 66645797, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.7 g of potassium t-butoxide (15.1 mmol) in tetrahydrofuran (100 ml) was added to a solution of 4.2 g of {2-[(2-bromoacetyl)-(3-fluoro-2-methylphenyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl ester obtained in Example (67b) (10.1 mmol) in tetrahydrofuran (100 ml) under a nitrogen atmosphere and under cooling in a dry ice-acetone bath over 30 minutes, and the mixture was stirred at the same temperature for 10 minutes. A saturated ammonium chloride aqueous solution was added to the reaction mixture. The mixture was returned to room temperature and diluted with water, followed by extraction with ethyl acetate. Then, the organic layer was 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:methylene chloride/ethyl acetate=5/1) to obtain 1.6 g of the title compound (yield: 47%).

Workup

  1. temperatureunder cooling in a dry ice-acetone bath over 30 minutes
  2. customwas returned to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThen, the organic layer was dried 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:methylene chloride/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-81c45682b9414e32a8ed27d56178777e
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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