Acetic Acid → HCID 69543941, compound

Participants

Reaction Steps

To a solution of 3-t-butyldiphenylsilyloxy-1-{4-[(3S)-1-(p-nitrobenzyloxycarbonyl)-pyrrolidin-3-ylcarbamoyl]-1,3-thiazol-2-yl}azetidine (560 mg, 0.816 mmol) (obtained as described in Reference Example 52(5)) in anhydrous tetrahydrofuran (17 ml) was added successively acetic acid (56 μl, 0.980 mmol) and a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (980 μl, 0.980 mmol) in an ice bath. The mixture was stirred in the ice bath for 1.5 hours. After checking the completion of the reaction, ethyl acetate and water were added thereto and the aqueous layer was extracted with ethyl acetate. The obtained organic layer was washed successively with 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 ethyl acetate→ethyl acetate:methanol (95:1) as the eluant to afford 3-hydroxy-1-{4-[(3S)-1-(p-nitrobenzyloxycarbonyl)-pyrrolidin-3-ylcarbamoyl]-1,3-thiazol-2-yl}azetidine (359 mg, yield 98%) as a white solid.

Provenance & Evidence