Hydrochloric Acid → [4-(2-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethoxy)-2-fluorophenyl]acetic acid

Participants

Reaction Steps

To a solution of methyl [4-(2-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethoxy)-2-fluorophenyl]acetate (1.50 g, 3.25 mmol) in 21 ml of tetrahydrofuran was added 14 ml of methanol and 14 ml of water. Lithium hydroxide (0.401 g, 16.7 mmol) was added to the reaction mixture, and the reaction mixture was stirred at RT overnight. 1 M hydrochloric acid was added to adjust the pH to 4. The volatiles were removed under reduced pressure, and the remaining aqueous solution was extracted with dichloromethane (3×20 ml). The organic fractions were combined, dried over magnesium sulphate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Biotage 100 g) using a gradient eluent of 0-70% ethyl acetate in hexanes (700 ml) to afford the title compound. LC/MS (m/z) 434.1 (M+H)+.

Provenance & Evidence