Hydrochloric Acid → 1-[(2S)-1,4-Dioxan-2-ylmethyl]-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid

Participants

Reaction Steps

(2R)-1,4-Dioxan-2-ylmethyl methanesulfonate (95 mg) was added to a suspension of ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate (100 mg) and cesium carbonate (264 mg) in DMF (2 ml) at room temperature. The reaction mixture was stirred at room temperature overnight. (2R)-1,4-Dioxan-2-ylmethyl methanesulfonate (32 mg) was added at room temperature. The reaction mixture was stirred at 80° C. overnight. (2R)-1,4-Dioxan-2-ylmethyl methanesulfonate (32 mg) was added at room temperature. The reaction mixture was stirred at 100° C. for three hours and then returned to room temperature. A 1 N aqueous sodium hydroxide solution (2 ml) was added to the reaction mixture at room temperature. The reaction mixture was stirred at room temperature for one hour. A 1 N aqueous hydrochloric acid solution and water were added to the reaction mixture, and the precipitated solid was collected by filtration, washed with water and then dried to give 101 mg of the title compound as a solid.

Provenance & Evidence