Sodium Bicarbonate → HCID 10599948, compound

Participants

Reaction Steps

1-[(1R,2S)-2-(2-Fluorophenyl)-2-hydroxy-3-(isopropoxydimethylsilyl)-1-methylpropyl]-3-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2(1H,3H)-imidazolone (5.5 g) was dissolved in a mixture of methanol and tetrahydrofuran (1:1, 50 ml), to which 10 ml of 30% aqueous hydrogen peroxide and 0.82 g of sodium hydrogencarbonate were added. The mixture was heated at 80° to 85° C. for 2 hours. The reaction solution was cooled and extracted with 200 ml of ethyl acetate. The extract was washed with 100 ml of water, an aqueous solution of Na2S2O3 (100 ml×2) and 100 ml of an aqueous solution of sodium chloride successively, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent; hexane:ethyl acetate=1:1) and recrystallized from a mixture of methanol and diisopropyl ether to give 2.7 g of 1-[(1R,2S)-2-(2-fluorophenyl)-2,3-dihydroxy-1-methylpropyl]-3-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2(1H,3H)-imidazolone (yield: 60%) as colorless powdery crystals.

Provenance & Evidence