3-Methanesulfonyloxy-1-(4-pyrrolidinocarbonyl-1,3-thiazol-2-yl)azetidine → 3-Acetylthio-1-(4-pyrrolidinocarbonyl-1,3-thiazol-2-yl)azetidine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-methanesulfonyloxy-1-(4-pyrrolidinocarbonyl-1,3-thiazol-2-yl)azetidine (335 mg, 1.01 mmol) (obtained as described in Reference Example 26(3)) in dimethylformamide (15 ml) was added potassium thioacetate (1.10 g, 8.80 mmol) at room temperature, and the reaction mixture was stirred in an oil bath (80° C.) for 5 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by chromatography on a silica gel column using ethyl acetate as the eluant to afford 3-acetylthio-1-(4-pyrrolidinocarbonyl-1,3-thiazol-2-yl)azetidine (235 mg, yield 75%) as a pale brown solid.

Provenance & Evidence