Water → (3RS,4RS)-4-[3-oxo-3-(3-fluoro-6-methoxyquinolin-4-yl)-propyl]-1-[2-(2,5-difluoro-phenylsulfanyl)ethyl]piperidine-3-acetic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.3 g of methyl (3RS,4RS)-4-[3-oxo-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,5-difluorophenylsulfanyl)ethyl]piperidine-3-acetate in 1.34 cm3 of a 1N aqueous sodium hydroxide solution and 5 cm3 of dioxane is brought to a temperature in the region of 60° C. with stirring and under an inert atmosphere for 1 hour. After cooling to around 20° C., the reaction medium is evaporated to dryness under reduced pressure (2 kPa) at a temperature in the region of 50° C. The evaporation residue obtained is taken up with 20 cm3 of water and 20 cm3 of diethyl ether, and the aqueous phase is separated after settling out and neutralized with 1.3 cm3 of 1N aqueous hydrochloric acid solution and is then extracted with 70 cm3 of ethyl acetate. The organic phase is dried over magnesium sulfate, filtered, and then evaporated according to the same conditions above. 0.23 g of (3RS,4RS)-4-[3-oxo-3-(3-fluoro-6-methoxyquinolin-4-yl)-propyl]-1-[2-(2,5-difluoro-phenylsulfanyl)ethyl]piperidine-3-acetic acid, in the form of a beige-colored solid, is obtained.

Provenance & Evidence