HCID 22242929, compound → HCID 22242754, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-methanesulfonyloxy-1-{4-[3-(p-nitrobenzyloxycarbonylamino)-azetidine-1-carbonyl]-1,3-thiazol-2-yl}azetidine (760 mg, 1.45 mmol) (obtained as described in Reference Example 57(6)) in dimethylformamide (38 ml) was added potassium thioacetate (993 mg, 8.70 mmol) at room temperature. The mixture was stirred in an oil bath (80° C.) for 9 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 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 ethyl acetate as the eluant to afford 3acetylthio-1-{4-[3-(p-nitrobenzyloxycarbonylamino)-azetidine-1-carbonyl]-1,3-thiazol-2-yl}azetidine (397 mg, yield 56%) as a pale brown solid.

Provenance & Evidence