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

Participants

Reaction Steps

Sodium hydroxide (61 mg) was added to a solution of ethyl 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-2-yl]propanoate (D114) (68 mg) in THF (5 mL), isopropanol (5 mL) and water (2.5 mL). The reaction mixture was stirred at room temperature overnight. The mixture was neutralized with 2M HCl till pH ˜6.0. The solvent was concentrated, and the residue was dissolved in water. The precipitated solid was purified by Mass Directed Auto Prep to afford 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-2-yl]propanoic acid (E89) (6 mg). δH (DMSO-d6, 400 MHz): 1.38 (6H, d), 2.69 (2H, t), 2.98 (2H, t), 4.97 (1H, m), 6.33 (1H, s), 7.44 (1H, d), 7.55 (1H, d), 7.75 (1H, dd), 8.21 (1H, s), 8.40 (1H, dd), 8.49 (1H, d), 11.34 (1H, s), 12.25 (1H, s); MS (ES): C23H20N4O4 requires 416; found 417.2 (M+H+).

Provenance & Evidence