반응 #89696

반응 방정식

N-benzyloxycarbonyl-β-alanine

NaH

benzyl bromide

→

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

용매

THF

DMF

반응 조건

후처리

1. 1
   기타at 0° C.
2. 2
   workup.STIRRINGThe reaction mixture was stirred at rt for 22 h
3. 3
   기타It was quenched with water (90 mL)
4. 4
   추출extracted three times with ethyl acetate
5. 5
   세척The combined organic layers were washed with brine
6. 6
   건조dried over MgSO4
7. 7
   여과filtered
8. 8
   농축concentrated under reduced pressure
9. 9
   기타The residue was purified by Combiflash (40-60% EtOAc/hexane)
10. 10
    기타to afford

실험 절차

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).

출처