反应详情

Methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2-[(tert-butoxycarbonyl)amino]butanoate was dissolved in 20 ml dichloromethane and 4 ml HCl in dioxane (4M) was added. The mixture was stirred 2 hours and concentrated down. The residue was washed with ether, then partition between 1M NaOH and dichloromethane. The dichloromethane layer was removed and dried with MgSO4. Sodium triacetoxyborohydride (0.61 g, 2.9 mmol) and acetaldehyde (0.33 ml, 5.8 mmol) was added. The mixture was stirred 2 days and washed with 1M NaOH. The mixture was then concentrated and purified by silica gel chromatography (40% CH2Cl2/60% EtOAc) to afford methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydro-quinolin-1(2H)-yl]carbonyl}phenoxy)-2-(diethylamino)butanoate (0.075 g, 17%).

1. concentrationconcentrated down
2. washThe residue was washed with ether
3. custompartition between 1M NaOH and dichloromethane
4. customThe dichloromethane layer was removed
5. dry with materialdried with MgSO4
6. stirringThe mixture was stirred 2 days
7. washwashed with 1M NaOH
8. concentrationThe mixture was then concentrated
9. custompurified by silica gel chromatography (40% CH2Cl2/60% EtOAc)