反应详情

温度

60 °C

To a solution of ethyl 4-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]butanoate (D53) (40 mg) in THF (5 mL) was added aqueous NaOH (2 M, 2 mL). The reaction mixture was stirred at 60° C. overnight. The mixture was acidified with HCl (2 M) to pH 4-5, and then partitioned between ethyl acetate (25 mL) and water (25 mL). The organic phase was washed with water (25 mL) and 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 4-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]butanoic acid (E32) (22 mg). δH (DMSO-d6, 400 MHz): 1.36 (6H, d), 1.90 (2H, m), 2.28 (2H, t), 2.77 (2H, t), 4.89 (1H, m), 7.20 (1H, t), 7.26 (1H, d), 7.44 (1H, d), 7.80 (1H, d), 7.93 (1H, d), 8.20 (1H, dd), 8.37 (1H, d), 10.83 (1H, s), 12.05 (1H, br s). MS (ES): C23H22ClN3O4 requires 439; found 440.2 (M+H+).

1. custompartitioned between ethyl acetate (25 mL) and water (25 mL)
2. washThe organic phase was washed with water (25 mL) and brine (25 mL)
3. dry with materialdried over anhydrous sodium sulphate
4. customevaporated
5. customto give the crude product, which
6. customwas purified by Mass Directed Auto Prep