Sodium Hydroxide → HCID 44548061, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 5-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]pentanoate (D56) (120 mg) in tetrahydrofuran (5 mL) and methanol (5 mL) stirred at 20° C. was added a solution of sodium hydroxide (40 mg) in water (5 mL) in one charge. The reaction mixture was stirred at 20° C. for 8 hours. The reaction mixture was concentrated and then H2SO4 (0.1 M) solution was added dropwise to pH around 3. Extracted with EtOAc (100 mL), the organic layer was separated and the organic solvent was evaporated off. The residue was purified by Mass Directed Auto Prep to afford 5-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]pentanoic acid (E34) (70 mg). δH (DMSO-d6, 400 MHz): 1.37 (6H, d), 1.57-1.71 (4H, m), 2.27 (2H, t), 2.77 (2H, t), 4.88-4.92 (1H, m), 7.21 (1H, t), 7.26 (1H, d), 7.47 (1H, d), 7.80 (1H, d), 7.94 (1H, dd), 8.21 (1H, dd), 8.39 (1H, d), 10.82 (1H, s), 12.00 (1H, br s). MS (ES): C24H24ClN3O4 requires 453. found 454.2 (M+H+).

Provenance & Evidence