Tert-butyl [(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)oxy]acetate → [(3-{5-[2-(Methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)oxy]acetic acid

Participants

Reaction Steps

Tert-butyl [(3-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)oxy]acetate (411 mg, 0.82 mmol) was dissolved in a 4M solution of HCl in dioxane (5 mL). The resulting mixture was stirred at RT for 5 hours. The reaction mixture was concentrated under reduced pressure to give the title compound as a colorless oil (298 mg, 82%). 1H NMR (DMSO-d6, 300 MHz): d=12.75 (brs, 1H), 8.33 (d, J=1.5 Hz, 1H), 8.18 (dd, J=7.9, 1.8 Hz, 1H), 8.13 (brs, 1H), 8.06 (m, 1H), 7.61 (m, 2H), 7.43 (d, J=8.0H, 1H), 7.37-7.26 (m, 3H), 7.15 (d, J=7.0 Hz, 1H), 4.68 (s, 2H), 4.23 (d, 2H), 4.17 (d, J=12.7 Hz, 1H), 4.17 (d, J=12.7 Hz, 1H), 4.16 (s, 2H), 3.25 (s, 3H), 2.04 (s, 3H). LC/MS (Method A): 445.3 (M+H)+. 443.4 (M−H)−. HPLC (Method A) Rt: 5.18 min (purity: 97.5%).

Provenance & Evidence