Acetic Acid → HCID 69543973, compound

Participants

Reaction Steps

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-[(3R)-1-(p-nitrobenzyloxycarbonyl)-pyrrolidin-3-ylcarbamoyl]-1,3-oxazol-2-yl}azetidine (810 mg, 1.21 mmol) (obtained as described in Reference Example 77(1)) in anhydrous tetrahydrofuran (40 ml) was added a solution of acetic acid (83 μl, 1.45 mmol) and 1.0 M tetra-n-butylammonium fluoride in tetrahydrofuran (1.45 ml, 1.45 mmol) in an ice bath and the mixture was stirred in an ice bath overnight. 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 ethyl acetate→ethyl acetate:methanol (95:5) as the eluant to afford 3-hydroxy-1-{4-[(3R)-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylcarbamoyl]-1,3-oxazol-2-yl}azetidine (507 mg, yield 97%) as a pale yellow oil.

Provenance & Evidence