tert-Butyl hydroperoxide → 3-[2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-methylsulfinylbenzoylamino]-N-(5-chloropyridin-2-yl)-pyridine-2-carboxamide

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Reaction Steps

3-[2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-(methylthio)benzoylamino]-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide (2.19 g, 3.66 mmol) was diluted with chloroform (20 mL). Camphorsulfonic acid (179 mg, 0.77 mmol) was added, followed by a solution of t-butyl hydroperoxide (0.75 mL, 7.50 mmol). After stirring overnight, the reaction was concentrated and purified by flash column chromatography (about 225 g silica, 10% EtOAc/CH2Cl2 through 10% MeOH/CH2Cl2) to give the desired product as a white solid (1.775 g, 2.89 mmol, 79%).

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