Methanol → 2-(2-fluoro-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)-N-(4-(5-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)benzamido)acetic acid

Participants

Reaction Steps

Prepared using General Procedure 9. To a stirring solution of methyl 2-(2-fluoro-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)-N-(4-(5-(4′-methyl-[1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)benzamido)acetate INT-79 (91 mg, 0.119 mmol) in THF (2 mL) and MeOH (0.25 mL) was added 1 M LiOH (146 μL, 0.146 mmol). The reaction mixture was stirred at room temperature for 18 h. The solvent was removed and the residue suspended in water (5 mL). The mixture was acidified to pH 1 using 1 M HCl, filtered under vacuum and the captured solid washed with MeOH (1 mL). The captured solid was triturated with diethyl ether (3 mL) to afford 25 mg (28%) of 2-(2-fluoro-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)-N-(4-(5-(4′-methyl-[1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)benzamido)acetic acid 496. LCMS-ESI (m/z) calculated for C41H32F4N4O6: 752; found 753 [M+H]+, tR=9.64 min (Method 9). 1H NMR (400 MHz, DMSO) δ 10.18 (s, 1H), 8.35-8.18 (m, 2H), 8.07 (d, J=7.8 Hz, 2H), 7.98-7.86 (m, 2H), 7.73-7.65 (m, 2H), 7.64-7.39 (m, 5H), 7.39-7.33 (m, 2H), 7.30 (d, J=8.2 Hz, 1H), 7.25-7.17 (m, 2H), 4.82 (br, 2H), 3.96-3.78 (m, 5H), 3.42 (br, 2H), 2.40 (s, 3H).

Provenance & Evidence