Hydrochloric Acid → HCID 44547913, compound

Participants

Reaction Steps

Sodium hydroxide (114 mg) was added to a solution of 2-methylpropyl 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-(2-methylpropyl)-1H-indol-3-yl]propanoate (D124) (77 mg) in THF (5 mL), isopropanol (4 mL) and water (2 mL). The reaction mixture was stirred at room temperature overnight. The mixture was neutralized with 2 M 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-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-(2-methylpropyl)-1H-indol-3-yl]propanoic acid (E30) (42 mg). δH (DMSO-d6, 400 MHz): 0.52 (6H, d), 1.37 (6H, d), 1.51 (1H, m), 2.61 (2H, t), 2.99 (2H, t), 3.99 (2H, d), 4.89 (1H, m), 7.19 (1H, t), 7.22 (1H, s), 7.45 (2H, m), 7.82 (1H, dd), 8.14 (1H, dd), 8.21 (1H, d), 12.04 (1H, br s); MS (ES): C26H28ClN3O4 requires 481; found 482.2 (M+H+).

Provenance & Evidence