Triethylamine → HCID 22243065, compound

Participants

Reaction Steps

To a solution of 3-hydroxy-1-{4-[2-(p-nitrobenzyloxycarbonylamino)ethylcarbamoyl]-1,3-thiazol-2-yl}azetidine (658.4 mg, 1.56 mmol) (obtained as described in Reference Example 56(5)) in a mixture of methylene chloride (33 ml) and pyridine (5 ml) were added methanesulfonyl chloride (0.31 ml, 4.00 mmol) and triethylamine (0.57 ml, 4.09 mmol) in an ice bath. After stirring the mixture in the ice bath for 10 minutes, the resulting mixture was stirred at room temperature 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 successively with 0.5M aqueous hydrochloric acid solution, 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 toluene:acetonitrile (1:2) as the eluant to afford 3-methanesulfonyloxy-1-{4-[2-(p-nitrobenzyloxycarbonylamino)-ethylcarbamoyl]-1,3-thiazol-2-yl}azetidine (607.3 mg, yield 78%) as a pale yellow solid.

Provenance & Evidence