Sodium Hydroxide → 3-(7-{5-[6-[(1-methylethyl)oxy]-5-(trifluoromethyl)-3-pyridinyl]-1,2,4-oxadiazol-3-yl}-1H-indol-3-yl)propanoic acid

Participants

Reaction Steps

Sodium hydroxide (50 mg) was added to a solution of ethyl 3-(7-{5-[6-[(1-methylethyl)oxy]-5-(trifluoromethyl)-3-pyridinyl]-1,2,4-oxadiazol-3-yl}-1H-indol-3-yl)propanoate (D37) (83 mg) in isopropanol (5 mL), THF (3 mL), water (1.5 mL). The reaction mixture was stirred at room temperature overnight. The organic solvents were removed. 2 M HCl was used to adjust the pH value to around 6.0. The crude product was purified by Mass Directed Auto Prep to afford 3-(7-{5-[6-[(1-methylethyl)oxy]-5-(trifluoromethyl)-3-pyridinyl]-1,2,4-oxadiazol-3-yl}-1H-indol-3-yl)propanoic acid (E15) (40 mg). δH (DMSO-d6, 400 MHz): 1.41 (6H, d), 2.64 (2H, t), 3.01 (2H, t), 5.56 (1H, m), 7.22 (1H, t), 7.29 (1H, d), 7.84 (1H, d), 7.96 (1H, dd), 8.79 (1H, d), 9.36 (1H, d), 10.86 (1H, s), 12.07 (1H, br s); MS (ES): C22H19F3N4O4 requires 460; found 461.2 (M+H+).

Provenance & Evidence