Tetrabutylammonium Fluoride → HCID 497415, compound

Participants

Reaction Steps

3-(4-(4-t-Butyldimethylsilyloxymethylimidazol-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one (0.59 g, 1.2 mmol) in anhydrous tetrahydrofuran (15 ml) was cooled to 0°. A solution of tetra-n-butylarnmonium fluoride (1 M, 5 ml, 5 mmol) was added and the mixture stirred 3 hours as the temperature rose to ambient. The mixture was evaporated to drvness, redissolved in dichloromethane (50 ml), washed with water (3×25 ml), and dried over magnesium sulfate. After filtration and evaporation the residue was purified by chromatography on a 10 g silica Mega Bond Elut® column. cluting with a gradient increasing in polarity from 0 to 10% MeOH in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (245 mg). MS (ESP): 375 (MH+) for C17H15FN4O5.

Provenance & Evidence