Acetic Acid → HCID 22242799, compound

Participants

Reaction Steps

To a solution of 3-t-butyldiphenylsilyloxy-1-{4-[3-(p-nitrobenzyloxycarbonylamino)-azetidine-1-carbonyl]-1,3-thiazol-2-yl}azetidine (850 mg, 1.27 mmol) (obtained as described in Reference Example 57(4)) in anhydrous tetrahydrofuran (43 ml) were added successively acetic acid (87 μl, 1.52 mmol) and a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (1.52 ml, 1.52 mmol) in an ice bath. The mixture was stirred in the ice bath for 30 minutes. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and water. 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. To the residue were added ethyl acetate and diisopropyl ether, and the resulting mixture was filtered off and washed with diisopropyl ether to give 3-hydroxy-1-{4-[3-(p-nitrobenzyloxycarbonylamino)-azetidine-1-carbonyl]-1,3-thiazol-2-yl}azetidine (486 mg, yield 88%) as a white solid.

Provenance & Evidence