HCID 22242812, compound → HCID 22242934, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-methanesulfonyloxy-1-(4-p-nitrobenzyloxycarbonyl-1,3-thiazol-2-yl)piperidine (1.2 g, 2.72 mmol) (obtained as described in Reference Example 14(5)) in dimethylformamide (60 ml) was added potassium thioacetate (625 mg, 5.47 mmol) at room temperature, and the reaction mixture was stirred in an oil bath (90° C.) for 3.5 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (1:1) as the eluant to afford 4-acetylthio-1-(4-p-nitrobenzyloxycarbonyl-1,3-thiazol-2-yl)piperidine (769 mg, yield 88%) as a pale brown solid.

Provenance & Evidence