Hydrochloric Acid → 4-[(1S)-1-({[5-Chloro-2-(3-chloro-2-methylphenoxy)pyridin-3-YL]carbonyl}amino)ethyl]benzoic acid

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A mixture of methyl 4-[(1S)-1-({[5-chloro-2-(3-chloro-2-methylphenoxy)pyridin-3-yl]carbonyl}amino)ethyl]benzoate (step 2, 230 mg, 0.56 mmol), N,N-dimethylformamide (5 mL), and 2 M sodium hydroxide aqueous solution (2.5 mL) was stirred at room temperature for 16 h. The mixture was poured into 2 M hydrochloric acid (30 mL), and extracted with ethyl acetate (100 mL×2). The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flush column chromatography on silica gel eluting with dichloromethane/methanol (20/1) to give 191 mg (86%) of the title compound as white solids: 1H-NMR (DMSO-d6) δ 9.06 (1H, d, J=7.9 Hz), 8.25 (1H, d, J=2.6 Hz), 8.15 (1H, d, J=2.6 Hz), 7.88 (2H, d, J=8.1 Hz), 7.53 (2H, d, J=8.2 Hz), 7.46–7.15 (1H, m), 5.24–5.14 (1H, m), 2.10 (3H, s), 1.47 (3H, d, J=6.9 Hz); MS (ESI) m/z 445 (M+H)+, 443 (M−H)−.

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