反应详情

2-(((tert-butyldimethylsilyl)oxy)methyl)acrylaldehyde (Intermediate 158, 4.76 g, 23.76 mmol) was added to a solution of (R)-tert-butyl (1-aminobut-3-en-2-yl)(benzyloxy)carbamate (Intermediate 156, 5.79 g, 19.80 mmol) in THF (100 mL), followed by addition of trimethylsilyl cyanide (10.62 mL, 79.19 mmol). The mixture was stirred at room temperature overnight. More TMS-CN was added and stirred longer until less starting material seen by LCMS. MgSO4 was added to the reaction mixture and stirred for 1 hr. Sodium bicarbonate (3.33 g, 39.58 mmol) was added, followed by (9H-fluoren-9-yl)methyl carbonochloridate (7.68 g, 29.69 mmol). The resulting mixture was stirred at room temperature overnight. 0.3 eq more FmocCl was added and stirred 5 h more. The mixture was filtered and the filtrate was evaporated. The residue was purified on silica gel column (0-22%, EtOAc/hexane) to afford the title compound (3.32 g, 23.18%) as a pale yellow thick oil.

1. stirringstirred longer until less starting material
2. stirringstirred for 1 hr
3. stirringThe resulting mixture was stirred at room temperature overnight
4. stirringstirred 5 h more
5. filtrationThe mixture was filtered
6. customthe filtrate was evaporated
7. customThe residue was purified on silica gel column (0-22%, EtOAc/hexane)