反应详情

D-alanine methyl ester hydrochloride (420 mg) and 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indole-3-carbaldehyde (D71) (382 mg) was added to a solution of NaOH (120 mg) in methanol (20 mL). After stirring for 0.5 hour, methanol was evaporated off. A solution of AcOH (0.5 mL) in dichloromethane (40 mL) was added to the residue. NaBH(OAc)3 (847 mg) was added to the above mixture. The reaction mixture was stirred at room temperature overnight, and quenched 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 methyl N-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]methyl}-D-alaninate (D75) (262 mg) as a white solid. MS (ES): C24H25ClN4O4 requires 468; found 491.1 (M+Na+).

1. custommethanol was evaporated off
2. additionA solution of AcOH (0.5 mL) in dichloromethane (40 mL) was added to the residue
3. additionNaBH(OAc)3 (847 mg) was added to the above mixture
4. stirringThe reaction mixture was stirred at room temperature overnight
5. customquenched by saturated NaHCO3 solution
6. customThe organic layer was separated
7. washwashed with water and brine
8. customAfter the solvent was evaporated off the residue
9. customwas purified by Mass Directed AutoPrep