Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 3-(3-hydroxy-cyclopentyl)-2-(4-methanesulfonyl-phenyl)-N-thiazol-2-yl-propionamide

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(4-methanesulfonyl-phenyl)-3-[3-(tetrahydropyran-2-yloxy)-cyclopentyl]-N-thiazol-2-yl-propionamide (450 mg, 0.94 mmol) in ethanol (9.4 mL) was treated with pyridinium p-toluenesulfonate (24 mg, 0.094 mmol). The resulting reaction mixture was heated at 60° C. for 4 h. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo. The resulting yellow residue was diluted with ethyl acetate (100 mL) and then washed with a saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 1/3 to 1/7 hexanes/ethyl acetate) afforded the 3-(3-hydroxy-cyclopentyl)-2-(4-methanesulfonyl-phenyl)-N-thiazol-2-yl-propionamide (318 mg, 86%) as a white foam: mp 69–72° C.; FAB-HRMS m/e calcd for C18H22N2O4S2 (M+H)+ 395.1099, 395.1091.

Provenance & Evidence