Acetic Acid → HCID 22242963, compound

Participants

Reaction Steps

To a solution of 3-t-butyldiphenylsilyloxy-1-{4-[N-isopropyl-N-(p-nitrobenzyloxycarbonylmethyl)carbamoyl]-1,3-thiazol-2-yl}azetidine (1.81 g, 2.69 mmol) (obtained as described in Reference Example 48(4)) in anhydrous tetrahydrofuran (90 ml) were added acetic acid (0.18 ml, 3.23 mmol) and a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (3.23 ml, 3.23 mmol) in an ice bath. The mixture was stirred in the ice bath for 2 hours. After checking the completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using methylene chloride:ethyl acetate (1:1) as the eluant to afford 3-hydroxy-1-{4-[N-isopropyl-N-(p-nitrobenzyloxycarbonylmethyl)carbamoyl]-1,3-thiazol-2-yl}azetidine (968 mg, yield 83%) as a white solid.

Provenance & Evidence