反应 #89696

反应方程式

N-benzyloxycarbonyl-β-alanine

NaH

benzyl bromide

→

3-{benzyl[(benzyloxy)cabonyl]amino}propanoic acid

溶剂

THF

DMF

反应条件

后处理

1. 1
   其他at 0° C.
2. 2
   workup.STIRRINGThe reaction mixture was stirred at rt for 22 h
3. 3
   其他It was quenched with water (90 mL)
4. 4
   萃取extracted three times with ethyl acetate
5. 5
   洗涤The combined organic layers were washed with brine
6. 6
   干燥dried over MgSO4
7. 7
   过滤filtered
8. 8
   浓缩concentrated under reduced pressure
9. 9
   其他The residue was purified by Combiflash (40-60% EtOAc/hexane)
10. 10
    其他to afford

实验过程

To a stirred solution of N-benzyloxycarbonyl-β-alanine (11.16 g, 50.00 mmol) in anhydrous THF (160 mL) and DMF (40 mL) at 0° C. was slowly added NaH (60% in oil, 6.000 g, 150.0 mmol). After stirring at 0° C. for 15 min, benzyl bromide (9.10 mL, 75.00 mmol) was added. The reaction mixture was stirred at rt for 22 h. It was quenched with water (90 mL), followed by 1 N HCl (110 mL), and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by Combiflash (40-60% EtOAc/hexane) to afford 3-{benzyl[(benzyloxy)cabonyl]amino}propanoic acid as a viscous pale yellow oil (14.2 g, 91% in yield). MS (ESI): 312.0 (M−H).

来源