Toluene → HCID 178475413, compound

Participants

Reaction Steps

To a solution of 4′-fluoro-5-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1′-biphenyl]-2-ol (390 mg) in pyridine (4 ml) was added dropwise acetic anhydride (0.135 ml) at room temperature, and the mixture was stirred for 4 h. Acetic anhydride (22.5 μl) was further added and the mixture was stirred for 15 h. The reaction mixture was subjected to azeotropic reaction with toluene for concentration, diluted with ethyl acetate, washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and to a solution of the residue (414 mg) in pyridine (4 ml) was added dropwise acetic anhydride (0.209 ml) at room temperature. The mixture was stirred for 15 h and the reaction mixture was subjected to azeotropic reaction with toluene for concentration. To a solution of the residue in methanol (15 ml) was added 0.1N aqueous p-toluenesulfonic acid solution (7.5 ml) at room temperature, and the mixture was stirred for 1 h. The reaction mixture was concentrated, diluted with ethyl acetate, neutralized with saturated aqueous sodium hydrogen carbonate, extracted with ethyl acetate, washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by column chomatography (eluent; ethyl acetate→ethyl acetate:methanol=20:1) to give the colorless amorphous title compound (337 mg).

Provenance & Evidence