[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:39]=[C:38]([S:40][CH3:41])[CH:37]=[CH:36][C:16]=2[C:17]([NH:19][C:20]2[C:21]([C:26]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=3)=[O:27])=[N:22][CH:23]=[CH:24][CH:25]=2)=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=[O:44].C(OO)(C)(C)C>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:39]=[C:38]([S:40]([CH3:41])=[O:44])[CH:37]=[CH:36][C:16]=2[C:17]([NH:19][C:20]2[C:21]([C:26]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=3)=[O:27])=[N:22][CH:23]=[CH:24][CH:25]=2)=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]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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