Water → HCID 86609415, compound

Participants

Reaction Steps

To a solution of (E)-3-{[1-(t-butoxycarbonyl)-1H-imidazol-5-yl]methylidene}-1-(triphenylmethyl)piperidin-4-ol (6.00 g) in toluene (100 ml) were added successively thioacetic acid (1.64 ml) and N,N-dimethylformamide dineopentyl acetal (6.40 ml) under ice-cooling, and the resulting mixture was stirred at room temperature for 1 hour. After stirring, water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate, hexane and dichloromethane (1:3:1) as the eluent to afford (E)-4-(acetylsulfanyl)-3-{[1-(t-butoxycarbonyl)-1H-imidazol-5-yl]methylidene}-1-(triphenylmethyl)piperidine (including impurities) as a yellow amorphous solid.

Provenance & Evidence