Sodium Hydroxide → Sodium 3-(4-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate

Participants

Reaction Conditions

Reaction Steps

To a suspension of ethyl 3-(4-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate (D72) (81 mg, 0.17 mmol) in ethanol (8 mL) was added aqueous sodium hydroxide (2M, 0.8 mL, 1.6 mmol) and the reaction heated to 50° C. to dissolve the reagents before heating at 40° C. for 1 h. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (20 mL) and water (20 mL) and acidified with aqueous hydrochloric acid (2M). The aqueous phase was extracted with further ethyl acetate (2×20 mL) and the combined organic extracts dried (phase separator) and concentrated in vacuo. The solid was then dissolved in acetonitrile and water with addition of an equimolar amount of sodium hydroxide (2M) before the solution was freeze-dried to give the title compound (57 mg). δH (d6-DMSO, 400 MHz): 8.44 (1H, dd), 8.35 (1H, d), 7.93 (1H, dd), 7.74 (1H, d), 7.65-7.54 (2H, m), 7.31 (1H, app. t), 7.00 (1H, dd) 4.99 (1H, septet), 4.38 (2H, t), 2.34 (2H, t), 1.36 (6H, d). MS (ES): C23H20F3N3O4 requires 459; found 460 (MH+).

Provenance & Evidence