Hydrogen Peroxide → Bicalutamide

Temperature

5 °C

To a solution of 2 g (2.51 mmol) of N-[4-cyano-3-trifluoromethyl-phenyl]-3-[4-fluorophenyl-thio]-2-hydroxy-2-methyl-propionamide in 10 ml of acetonitrile, 20 ml of methanol and 0.6 ml of water 0.38 g (2.75 mmol) of potassium carbonate was added. The mixture was cooled to 5° C. and 10 ml of 30% aqueous hydrogen peroxide solution was added dropwise. The mixture was stirred at 25° C. overnight, then diluted with 100 ml of water and extracted twice with 100 ml of dichloromethane. The organic layer was washed with 50 ml of brine, dried over sodium sulfate and concentrated under diminished pressure. The residue was recrystallized from a 1:4 mixture of ethyl acetate/petroleum ether, which has a boiling range of 40–70° C. The yield was 1.53 g (70.83%).

1. extractionextracted twice with 100 ml of dichloromethane
2. washThe organic layer was washed with 50 ml of brine
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated under diminished pressure
5. customThe residue was recrystallized from a 1:4 mixture of ethyl acetate/petroleum ether, which

ORD record

ord-f348955382ac4a4fa025d231d34ea457

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07199257B1