反应详情

Ethyl glycinate hydrochloride (698 mg) and 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indole-3-carbaldehyde (D61) (396 mg) were added to a solution of NaOH (200 mg) in ethanol (10 mL). After stirring for 0.5 hour, ethanol was evaporated off and then Dichloromethane (40 mL) containing AcOH (0.5 mL) was added to the residue. NaBH(OAc)3 (1.06 g) was added to the above mixture. The reaction mixture was stirred at room temperature overnight and then terminated by saturated NaHCO3 solution. The organic layer was separated and washed with water and brine. After the solvent was evaporated off the residue was purified by Mass Directed AutoPrep to afford ethyl N-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]methyl}glycinate (D77) (283 mg) as a yellow solid. δH (CDCl3, 400 MHz): 1.29 (3H, t), 1.46 (6H, d), 1.84 (1H, br s), 3.48 (2H, s), 3.74 (2H, s), 4.03 (3H, s), 4.21 (2H, q), 4.71-4.74 (1H, m), 7.03 (1H, s), 7.07 (1H, d), 7.22 (1H, t), 7.58 (1H, dd), 7.89 (1H, dd), 8.08 (1H, dd), 8.26 (1H, d). MS (ES): C25H27ClN4O4 requires 482; found 380.2 (M—NHCH2COOEt+).

1. customethanol was evaporated off
2. additionDichloromethane (40 mL) containing AcOH (0.5 mL)
3. additionwas added to the residue
4. additionNaBH(OAc)3 (1.06 g) was added to the above mixture
5. stirringThe reaction mixture was stirred at room temperature overnight
6. customterminated by saturated NaHCO3 solution
7. customThe organic layer was separated
8. washwashed with water and brine
9. customAfter the solvent was evaporated off the residue
10. customwas purified by Mass Directed AutoPrep