Hydrochloric Acid → HCID 59146124, compound

Participants

Reaction Steps

To a suspension of ethyl 3-[5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-7-fluoro-1H-indol-2-yl]propanoate (D164) (240 mg) in isopropanol (15 mL) was added 20% sodium hydroxide (509 mg) solution, then the reaction mixture was stirred at room temperature overnight. The mixture was acidified with HCl (2 M) to pH 4. The solvent of the reaction was removed by evaporation. The residue was dissolved in DMF (5 mL), the precipitation was filtered then the filtrate was purified by Mass Directed Auto Prep to afford 3-[5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-7-fluoro-1H-indol-2-yl]propanoic acid (E112) (75.3 mg) as a white solid. δH (DMSO-d6, 400 MHz): 1.30 (6H, d), 2.65 (2H, t), 2.93 (2H, t), 4.8 (1H, m), 6.38 (1H, s), 7.36 (1H, d), 7.44 (1H, d), 8.01 (1H, s), 8.05 (1H, d), 8.11 (1H, s), 11.76 (1H, s), 12.20 (1H, s); δF (DMSO-d6, 376 MHz): −132.6; MS (ES): C22H19ClFN3O4 requires 443; found 444.2 (M+H+).

Provenance & Evidence