Hydrochloric Acid → 3-[7-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-4-fluoro-1H-indol-3-yl]propanoic acid

Participants

Reaction Conditions

Reaction Steps

Sodium hydroxide (30 mg) was added to a solution of ethyl 3-[7-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-4-fluoro-1H-indol-3-yl]propanoate (D47) (195 mg) in THF (3 mL) and water (3 mL). The reaction mixture was stirred at 90° C. for 1 hour. Then 0.5 M HCl was added until pH was about 6. The solvent was concentrated, and the residue was dissolved in water. The precipitated solid was purified by Mass Directed Auto Prep to afford 3-[7-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-4-fluoro-1H-indol-3-yl]propanoic acid (E21) (78 mg) as a white solid. δH (DMSO-d6, 400 MHz): 1.38 (6H, d), 2.62 (2H, t), 3.06 (2H, t), 4.99 (1H, m), 6.98 (1H, dd), 7.26 (1H, d), 7.55 (1H, d), 7.90 (1H, dd), 8.47 (1H, dd), 8.70 (1H, d), 11.12 (1H, s), 12.15 (1H, br s). δF (DMSO-d6, 376 MHz): −118.0. MS (ES): C23H19FN4O4 requires 434; found 435.1 (M+H+).

Provenance & Evidence