Tetrabutylammonium Fluoride → N-[((5S)-3-{2-Fluoro-4'-[5-(hydroxymethyl)-4,5-dihydroisoxazol-3-yl]-1,1'-biphenyl-4-yl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide

Participants

Reaction Steps

N-[((5S)-3-{4′-[5-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-4,5-dihydroisoxazol-3-yl]-2-fluoro-1,1′-biphenyl-4-yl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide (164 mg, 0.3 mmol) was dissolved in tetrahydrofuran (5 ml) at room temperature. A solution of tetrabutylammonium fluoride in tetrahydrofuran (1M; 0.3 ml, 0.3 mmol) was added and the reaction mixture stirred for 30 minutes. The solvent was removed in vacuo then dichloromethane (2 ml) added. Purification by chromatography (SiO2 10 g bond elut; 0 to 6% methanol/dichloromethane) yielded a white solid. This was washed with water (50 ml) to yield 37.9 mg (29%) of the desired compound.

Provenance & Evidence