Water → 4-((1S)-1-{[5-Cyano-2-(3-fluorophenoxy)benzoyl]amino}ethyl)benzoic acid

Participants

Reaction Steps

To a stirred solution of methyl 4-((1S)-1-{[5-cyano-2-(3-fluorophenoxy)benzoyl]amino}ethyl)benzoate (step 2, 200 mg, 0.47 mmol) in dichloromethane (10 mL) was added a solution of boron tribromide (1 M in dichloromethane, 0.95 mL, 0.95 mmol) dropwise at 0° C. The resulting mixture was stirred at room temperature for 6 h. The reaction mixture was poured into water (10 mL) and the whole was extracted with ethyl acetate (50 mL). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flush column chromatography on silica gel eluting with hexane/ethyl acetate (1/1) to afford 62 mg (33%) of the title compound as white solids: 1H-NMR (DMSO-d6) δ 12.86 (1H, br.s), 8.95 (1H, d, J=7.9 Hz), 8.04 (1H, d, J=2.2 Hz), 7.90 (1H, dd, J=8.6, 2.2 Hz), 7.81 (2H, d, J=8.3 Hz), 7.51–7.40 (3H, m), 7.12–6.90 (4H, m), 5.07 (1H, m), 1.37 (3H, d, J=6.9 Hz); MS (ESI) m/z 405 (M+H)+, 403 (M−H)−.

Provenance & Evidence