Water → 2-Fluoro-4-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzoic acid

Participants

Reaction Steps

A solution of methyl 2-fluoro-4-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzoate (16 g; 37 mmol) in THF (400 mL) and MeOH (400 mL) at RT was treated with NaOH (37 mL; 5 M; 184.99 mmol). The reaction mixture was stirred at RT for 12 hours. The reaction mixture was concentrated to give a yellow solid. Water (600 mL) was added and the aqueous phase was washed with EtOAc (250 mL). Then the aqueous phase was acidified with HCl cc until pH 2 and extracted with EtOAc (2×300 mL). Organics were washed with brine, dried over MgSO4 and concentrated affording the title compound as a beige solid (11.66 g, 75%). 1H NMR (DMSO, 400 MHz) δ 13.64 (br s, 1H), 8.33 (d, J=1.41 Hz, 1H), 8.17 (dd, J=7.92 Hz, 1.4 Hz, 1H), 8.13-8.03 (m, 2H), 7.96 (dd, J=11.10 Hz, 1.17 HZ, 1H), 7.43 (d, J=7.91 Hz, 1H), 7.37-7.27 (m, 3H), 7.15 (d, J=7.03 Hz, 1H), 4.25-4.14 (m, 2H), 3.25 (s, 3H), 2.04 (s, 3H). LC/MS (Method B): 419.1 (M+H)+; 417.2 (M−H)−. HPLC: Rt 5.19 min (Purity: 99.2%).

Provenance & Evidence