HCID 10091453, compound → 2-(3,4-dichloro-phenyl)-3-(2-oxo-cyclopentyl)-N-thiazol-2-yl-propionamide

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(3,4-dichloro-phenyl)-3-(2-hydroxy-cyclopentyl)-N-thiazol-2-yl-propionamide (prepared as in Example 25, 162.5 mg, 0.42 mmol) in methylene chloride (4.2 mL) was treated with pyridinium chlorochromate (20 wt. % on basic alumina, 545 mg, 0.50 mmol). The reaction mixture was stirred at 25° C. for 2 h. At this time, the reaction was filtered through a plug of celite (ethyl acetate as eluent). The filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 50/50 hexanes/ethyl acetate) afforded 2-(3,4-dichloro-phenyl)-3-(2-oxo-cyclopentyl)-N-thiazol-2-yl-propionamide (64.8 mg, 40.1%) as a light tan solid: mp 79–81° C.; EI-HRMS m/e calcd for C17H16Cl2N2O2S (M+H)+ 383.0383, found 383.0384.

Provenance & Evidence