Hydrochloric Acid → 3-(7-{5-[6-[(1-methylethyl)oxy]-5-(methyloxy)-3-pyridinyl]-1,2,4-oxadiazol-3-yl}-1H-indol-3-yl)propanoic acid

Participants

Reaction Conditions

Reaction Steps

Sodium hydroxide (40 mg) was added to a solution of ethyl 3-(7-{5-[6-[(1-methylethyl)oxy]-5-(methyloxy)-3-pyridinyl]-1,2,4-oxadiazol-3-yl}-1H-indol-3-yl)propanoate (D38) (280 mg) in THF (3 mL) and water (3 mL). The resulting mixture was heated at 90° C. for 1 hour. Then 0.5 M HCl solution 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-[6-[(1-methylethyl)oxy]-5-(methyloxy)-3-pyridinyl]-1,2,4-oxadiazol-3-yl}-1H-indol-3-yl)propanoic acid (E18) (145 mg) as a white solid. δH (DMSO-d6, 400 MHz): 1.36 (6H, d), 2.63 (2H, t), 3.00 (2H, t), 3.96 (3H, s), 5.43 (1H, m), 7.22 (1H, t), 7.27 (1H, d), 7.82 (1H, d), 7.92 (1H, d), 7.95 (1H, d), 8.68 (1H, d), 10.79 (1H, s), 12.10 (1H, br s). MS (ES): C22H22N4O5 requires 422; found 423.2 (M+H+).

Provenance & Evidence