Water → 5-Fluoro-2-hydroxy-3-(2,2,2-trifluoroethylcarbamoyl)-benzoic acid-(2,3,4-trihydroxybutyl)amide

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Reaction Steps

6.95 g (13.5 mmol) of 2 benzyloxy-5-fluoro-3-(2,2,2-trifluoroethylcarbamoyl)-benzoic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethylamide] is dissolved in 20 ml of methanol, 5 ml of water and 5 ml of IN hydrochloric acid is added and stirred for 3 hours at room temperature. The solution is then adjusted to pH 6.3 by addition of anion exchanger Amberlite IRA 67, 200 mg of palladium-carbon (10%) is added and hydrogenated for 1 hour at normal pressure. The catalyst is then filtered off, the filtrate is evaporated to dryness in a vacuum and the residue is chromatographed on silica gel 60 (Merck) with dichloromethane/methanol. 3.76 g (9.77 mmol)=72.4% of the theoretical yield of the compound is obtained as an amorphous solid.

Provenance & Evidence