تفاعل #46647

معادلة التفاعل

(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

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe mixture was filtered
2. 2
   workup.ADDITIONthe filtrate was treated with MgSO4
3. 3
   ترشيحfiltered again
4. 4
   تركيزthe final filtrate was concentrated
5. 5
   أخرىThe resulting crude material was submitted to a Biotage purification (350 g silica gel, CH2Cl2 elution)

الإجراء التجريبي

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.

المصدر