Hydrochloric Acid → (5R)-3-(4-Ethynyl-3-fluorophenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one

Participants

Reaction Steps

(5R)-3-{3-Fluoro-4-[(trimethylsilyl)ethynyl]phenyl}-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (Intermediate 17, 6.1 g, 17 mmol) was stirred in methanol (155 ml). 1 N Potassium hydroxide (30 ml) was added and the reaction was stirred for 20 minutes. The solution was diluted with methylene chloride (200 ml) then acidified to pH 1.5 using 1 N hydrochloric acid. The solution was diluted with water and the compound was extracted using methylene chloride. The organic layer was washed with water, dried (magnesium sulfate), filtered, and concentrated. The orange solid was adsorbed onto silica gel and chromatographed using ethyl acetate to give the title compound as a yellow solid (2.3 g).

Provenance & Evidence