Acetic Acid → HCID 22242864, compound

Participants

Reaction Steps

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-{N-methyl-N-[2-(p-nitrobenzyloxycarbonylamino)-ethyl]carbamoyl}-1,3-thiazol-2-yl)azetidine (806.9 mg, 1.20 mmol) (obtained as described in Reference Example 58(3)) in anhydrous tetrahydrofuran (40 ml) were added successively acetic acid (0.09 ml, 1.57 mmol) and a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (1.44 ml, 1.44 mmol) in an ice bath, and then the mixture was stirred in the ice bath 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 obtained organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate: methanol (15:1) as the eluant to afford 3-hydroxy-1-(4-{N-methyl-N-[2-(p-nitrobenzyloxycarbonylamino)-ethyl]carbamoyl}-1,3-thiazol-2-yl)azetidine (428.2 mg, yield 84%) as a white solid.

Provenance & Evidence