Triethylamine → 1-(4-Morpholinocarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine

Participants

Reaction Steps

To a solution of 1-(4-morpholinocarbonyl-1,3-thiazol-2-yl)-3-hydroxyazetidine (540 mg, 2.01 mmol) (obtained as described in Reference Example 11(2)) in methylene chloride (27 ml) were added methanesulfonyl chloride (0.467 ml, 6.03 mmol) and triethylamine (0.845 ml, 6.03 mmol) in an ice bath. The reaction mixture was brought to room temperature in 10 minutes, and stirred for 1 hour. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The obtained 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 5% methanol in ethyl acetate as the eluant to afford 1-(4-morpholinocarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (688 mg, yield 99%) as a pale yellow solid.

Provenance & Evidence