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

Participants

Reaction Steps

Prepared using General Procedure 9. To a stirring solution of tert-butyl 2-(4-(2-(2,5-dimethoxyphenyl)acetamido)-N-(4-(3-(4′-methyl-[1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-5-yl)benzyl)benzamido)acetate INT-65 (55 mg, 0.073 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 20 h and a precipitate was formed. The mixture was filtered under vacuum and the captured solid washed with diethyl ether (5 mL). The captured solid was under vacuum to provide 36 mg (71%) of 2-(4-(2-(2,5-dimethoxyphenyl)acetamido)-N-(4-(3-(4′-methyl-[1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-5-yl)benzyl)benzamido)acetic acid 457 as a white solid. LCMS-ESI (m/z) calculated for C41H36N4O7: 696; found 697 [M+H]+, tR=9.84 min (Method 9). 1H NMR (400 MHz, DMSO) δ 9.89 (s, 1H), 8.22-8.11 (m, 4H), 7.87 (d, J=8.4 Hz, 2H), 7.66 (d, J=8.1 Hz, 2H), 7.60 (d, J=8.6 Hz, 4H), 7.51 (d, J=8.0 Hz, 2H), 7.33 (d, J=7.9 Hz, 2H), 6.94-6.90 (m, 1H), 6.88 (d, J=3.1 Hz, 1H), 6.83-6.78 (m, 1H), 4.81 (s, 2H), 3.75 (s, 3H), 3.72 (s, 3H), 3.64 (s, 2H), 3.48 (s, 2H), 2.39 (s, 3H).

Provenance & Evidence