Hydrochloric Acid → ({2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]ethyl}oxy)acetic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl ({2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]ethyl}oxy)acetate (D104) (20 mg) in THF (5 mL) was added aqueous NaOH (2 M, 1 mL). The reaction was stirred at 20° C. for 4 h. The mixture was acidified with aqueous HCl (2 M) to pH 4-5. After concentration, the residue was partitioned between ethyl acetate (25 mL) and water (25 mL). The organic phase was washed with brine (25 mL), dried over anhydrous sodium sulphate and evaporated to give the crude product, which was purified by Mass Directed Auto Prep to afford ({2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]ethyl}oxy)acetic acid (E79) (11 mg). δH (DMSO-d6, 400 MHz): 1.36 (6H, d), 2.98 (2H, t), 3.63 (3H, s), 3.74 (2H, t), 4.05 (2H, s), 4.89 (1H, m), 7.17 (1H, t), 7.26 (1H, s), 7.44 (2H, m), 7.81 (1H, dd), 8.13 (1H, dd), 8.19 (1H, d), 12.57 (1H, br s). MS (ES): C24H24ClN3O6 requires 469; found 470.2 (M+H+).

Provenance & Evidence