反应 #2122528

反应方程式

(S)-1-benzyl 4-methyl 2-aminosuccinate

9-bromo-9-phenyl-9H-fluorene

Et3N

→

(S)-1-benzyl 4-methyl 2-(9-phenyl-9H-fluoren-9-ylamino)succinate

溶剂

CH2Cl2

反应条件

后处理

1. 1
   过滤The mixture was filtered
2. 2
   workup.ADDITIONthe filtrate was treated with MgSO4
3. 3
   过滤filtered again
4. 4
   浓缩the final filtrate was concentrated
5. 5
   其他The resulting crude material was submitted to a Biotage purification (350 g silica gel, CH2Cl2 elution)

实验过程

Pb(NO3)2 (6.06 g, 18.3 mmol) was added over 1 min to a CH2Cl2 (80 mL) solution of (S)-1-benzyl 4-methyl 2-aminosuccinate (4.50 g, 19.0 mmol), 9-bromo-9-phenyl-9H-fluorene (6.44 g, 20.0 mmol) and Et3N (3.0 mL, 21.5 mmol), and the heterogeneous mixture was stirred at ambient condition for 48 hr. The mixture was filtered and the filtrate was treated with MgSO4 and filtered again, and the final filtrate was concentrated. The resulting crude material was submitted to a Biotage purification (350 g silica gel, CH2Cl2 elution) to afford (S)-1-benzyl 4-methyl 2-(9-phenyl-9H-fluoren-9-ylamino)succinate as highly viscous colorless oil (7.93 g). 1H NMR (DMSO-d6, δ=2.5 ppm, 400 MHz): δ 7.82 (m, 2H), 7.39-7.13 (m, 16H), 4.71 (d, J=12.4, 1H), 4.51 (d, J=12.6, 1H), 3.78 (d, J=9.1, NH), 3.50 (s, 3H), 2.99 (m, 1H), 2.50-2.41 (m, 2H, partially overlapped with solvent). LC (Cond. 1): RT=2.16 min; LC/MS: Anal. Calcd. for [M+H]+ C31H28NO4: 478.20; found 478.19.

来源