m-Chloroperbenzoic acid → methyl 3-[4-methoxy-3-[N-(4-trifluoromethylbenzyl)]carbamoylphenyl]-2-(methylsulfinyl)-propionate

Participants

Reaction Steps

To a solution of 1.50 g of methyl 3-[4-methoxy-3-[N-(4-trifluoromethylbenzyl)]carbamoylphenyl]-2-(methylthio)propionate in 30 ml of methylene chloride were added 800 mg of mCPBA under cooling with ice, and the mixture was stirred for 30 minutes. The reaction mixture was washed with saturated aqueous solution of sodium bicarbonate and saturated brine in sequence and dried over anhydrous sodium sulfate. Solvent was distilled off under reduced pressure, and the residue obtained was purified by means of column chromatography (silica gel, methylene chloride:methanol=100:1 to 50:1) to obtain 1.22 g of methyl 3-[4-methoxy-3-[N-(4-trifluoromethylbenzyl)]carbamoylphenyl]-2-(methylsulfinyl)-propionate as colorless crystals. To a solution of 1.02 g of methyl 3-[4-methoxy-3-[N-(4-trifluoromethylbenzyl)]-carbamoylphenyl]-2-(methylsulfinyl)propionate obtained in 20 ml of methylene chloride were added 550 mg of mCPBA under cooling with ice, and the mixture was stirred for 7 hours at room temperature. The reaction mixture was washed with saturated aqueous solution of sodium bicarbonate and saturated brine in sequence and dried over anhydrous sodium sulfate. Solvent was distilled off under reduced pressure, and the crystals obtained were recrystallized from hexane-ethyl acetate to obtain 750 mg of methyl 3-[4-methoxy-3-[N-(4-trifluoromethylbenzyl)]carbamoylphenyl]-2-(methylsulfonyl)propionate as colorless crystals. Melting point 144-145° C.

Provenance & Evidence