Potassium ethanethioate → HCID 58595171, compound

Participants

Reaction Steps

To a solution of (3R)-1-(4-carbamoyl-1,3-thiazol-2-yl)-3-methanesulfonyloxypyrrolidine (190 mg, 0.652 mmol) (obtained as described in Reference Example 18(7)) in acetonitrile (6 ml) was added potassium thioacetate (223 mg, 1.96 mmol) at room temperature. The mixture was heated under reflux for 4 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 sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (1:1)→ethyl acetate→2% methanol in ethyl acetate as the eluant to afford (3S)-3-acetylthio-1-(4-carbamoyl-1,3-thiazol-2-yl)pyrrolidine (135 mg, yield 77%) as a pale brown solid.

Provenance & Evidence