Sodium Hydroxide → 5-[(2,5-Difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methyl-N-[3-(methylsulfinyl)propyl]pyridine-2-carboxamide

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Reaction Steps

To a solution of 5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methyl-N-[3-(methylthio)propyl]pyridine-2-carboxamide (149 mg, 0.293 mmol) in methylene chloride (5 ml), 3-chloroperbenzoic acid (51 mg, 0.293 mmol) was added under ice cooling, and the mixture was stirred for 30 minutes. 3-Chloroperbenzoic acid (20 mg, 0.116 mmol) was added to the reaction solution under ice cooling, and the resulting mixture was stirred for 15 minutes. 1 N aqueous sodium hydroxide was added to the reaction solution, and the mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The resulting concentration residue was subjected to silica gel column chromatography, and the fraction obtained from an elution with methanol:methylene chloride (=1:30) was concentrated under reduced pressure. Ethylacetate-hexane was added to the resulting concentration residue, and the solid thus precipitated was collected by filtration, to obtain the title compound (122 mg, 0.232 mmol, 79%) as a white powder.

Provenance & Evidence