1-(4-Morpholinocarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine → 3-Acetylthio-1-(4-morpholinocarbonyl-1,3-thiazol-2-yl)azetidine

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(4-morpholinocarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (680 mg, 1.96 mmol) (obtained as described in Reference Example 11(3)) in dimethylformamide (20 ml) was added potassium thioacetate (671 mg, 5.87 mmol) at room temperature, and then the reaction mixture was stirred in an oil bath (80° C.) for 18 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution. The obtained 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 residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (1:3)→ethyl acetate as the eluant to afford 3-acetylthio-1-(4-morpholinocarbonyl-1,3-thiazol-2-yl)azetidine (411 mg, yield 64%) as a pale brown solid.

Provenance & Evidence