Acetic Anhydride → HCID 18668579, compound

Participants

Reaction Steps

To a solution of 1-[6-[(diphenylmethylene)amino]-4′-fluoro[1,1′-biphenyl]-3-yl]-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (110 mg) in THF-methanol (1:1) (6 ml) were added anhydrous sodium acetate (29.6 mg) and hydroxyammonium chloride (18.7 mg) at room temperature, and the mixture was stirred for 22 h. The reaction mixture was concentrated, diluted with ethyl acetate, washed with 0.5N aqueous sodium hydroxide solution and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a crude product (118 mg) of 1-[6-amino-4′-fluoro[1,1′-biphenyl]-3-yl]-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol as a yellow oil. To a solution of this product (116 mg) and pyridine (29.6 μl) in THF (2 ml) was added dropwise acetic anhydride (28.3 μl) at 0° C., and the mixture was stirred at room temperature for 16 h. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture and the mixture was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chomatography (eluent; hexane:ethyl acetate=3:1→3:2) to give the colorless amorphous title compound (79.6 mg).

Provenance & Evidence