反应详情

温度

50 °C

To a solution of methyl (2R)-3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]-2-methylpropanoate (D60) (80 mg) in THF (5 mL) was added aqueous NaOH (2 M, 1 mL). The reaction was stirred at 50° C. for 16 h. The mixture was acidified with aqueous HCl (2 M) to pH 4-5, partitioned between ethyl acetate (50 mL) and water (50 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 (2R)-3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]-2-methylpropanoic acid (E36) (50 mg). δH (DMSO-d6, 400 MHz): 1.11 (3H, d), 1.35 (6H, d), 2.75 (2H, m), 3.04 (1H, m), 3.62 (3H, s), 4.88 (1H, m), 7.17 (2H, m), 7.43 (2H, m), 7.79 (1H, d), 8.13 (1H, dd), 8.20 (1H, d), 12.13 (1H, br s). MS (ES): C24H24ClN3O4 requires 453; found 454.2 (M+H+).

1. custompartitioned between ethyl acetate (50 mL) and water (50 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