反応 #2122528

反応方程式

(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

溶媒

CH2Cl2

反応条件

後処理

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

実験手順

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.

出典