Dimethyl Sulfoxide → Tert-butyl 3-((3-((4-(piperidin-1-yl)-2-(4-(3-(trifluoromethyl)benzoyl)-pyridin-2-yl)phenyl)carbamoyl)benzyl)thio)propanoate

Participants

Reaction Steps

A −10° C. solution of 23 mg of tert-butyl 3-((3-((2-(4-(hydroxy(3-(trifluoromethyl)phenyl)methyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzyl)thio)propanoate 5.2d, 17 mg of diisopropylethylamine, and 10 mg of DMSO in 0.4 mL of dichloromethane was treated with 10 mg of pyridine sulfur trioxide complex. After stirring for 1 h the reaction mixture was applied directly to a silica gel column and eluted with a gradient of 0% to 10% ethyl acetate in dichloromethane. Evaporation of the solvent yielded 9.5 mg of product. MS (ES, m/z) 704.2 [M+H]+.

Provenance & Evidence