Imidazole → HCID 22242906, compound

Participants

Reaction Steps

To a solution of 3-hydroxy-1-{4-[N-(2-hydroxyethyl)-N-methyl-carbamoyl]-1,3-thiazol-2-yl}azetidine (576 mg, 2.24 mmol) (obtained as described in Reference Example 40(3)) in dimethylformamide (29 ml) were added t-butyldimethylsilyl chloride (354 mg, 2.35 mmol) and imidazole (160 mg, 2.35 mmol) in an ice bath, and then the reaction mixture was stirred in the ice bath for 2 hours. 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 hexane:ethyl acetate (3:1)→ethyl acetate as the eluant to afford 1-(4-{N-[2-(t-butyldimethylsilyloxy)-ethyl]-N-methyl-carbamoyl}-1,3-thiazol-2-yl)-3-hydroxyazetidine (489 mg, yield 60%) as a pale yellow solid.

Provenance & Evidence