تفاعل #89696

معادلة التفاعل

N-benzyloxycarbonyl-β-alanine

NaH

benzyl bromide

→

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

المذيبات

THF

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىat 0° C.
2. 2
   workup.STIRRINGThe reaction mixture was stirred at rt for 22 h
3. 3
   أخرىIt was quenched with water (90 mL)
4. 4
   استخلاصextracted three times with ethyl acetate
5. 5
   غسيلThe combined organic layers were washed with brine
6. 6
   تجفيفdried over MgSO4
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated under reduced pressure
9. 9
   أخرىThe residue was purified by Combiflash (40-60% EtOAc/hexane)
10. 10
    أخرىto afford

الإجراء التجريبي

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).

المصدر