Hydrochloric Acid → 4-[(1S)-1-[[5-chloro-2-(3-fluorophenoxy)pyridine-3-carbonyl]amino]ethyl]benzoic Acid

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl 4-[(1S)-1-({[5-chloro-2-(3-fluorophenoxy)pyridin-3-yl]carbonyl}amino)ethyl]benzoate (step 2, 180 mg, 0.42 mmol) in tetrahydrofuran (3 mL) was added 2 N sodium hydroxide aqueous The reaction mixture was stirred at 65° C. for 5 h. After cooling, the reaction mixture was acidified by the addition of 2 N hydrochloric acid (2 mL). The aqueous mixture was partitioned between water (50 mL) and dichloromethane (50 mL) and the organic phase was separated. The aqueous phase was extracted with dichloromethane (50 mL). The combined organic layer was washed with brine (100 mL), dried (sodium sulfate), and concentrated. The residual solids were recrystallized from ethyl acetate to afford 103 mg (60%) of the title compound as white solids: 1H-NMR (CDCl3) δ 8.56 (1H, d, J=3.0 Hz), 8.16 (1H, d, J=3.0 Hz), 8.08–8.05 (3H, m), 7.47–7.40 (3H, m), 7.07–6.91 (3H, m), 5.43–5.33 (1H, m), 1.60 (3H, d, J=7.1 Hz), a peak of COOH was not observed; MS (ESI) m/z 415 (M+H)+, 413 (M−H)−.

Provenance & Evidence