Réaction #89696

Équation de réaction

N-benzyloxycarbonyl-β-alanine

NaH

benzyl bromide

→

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

Solvants

THF

DMF

Conditions de réaction

Traitement

1. 1
   Autreat 0° C.
2. 2
   workup.STIRRINGThe reaction mixture was stirred at rt for 22 h
3. 3
   AutreIt was quenched with water (90 mL)
4. 4
   Extractionextracted three times with ethyl acetate
5. 5
   LavageThe combined organic layers were washed with brine
6. 6
   Séchagedried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated under reduced pressure
9. 9
   AutreThe residue was purified by Combiflash (40-60% EtOAc/hexane)
10. 10
    Autreto afford

Mode opératoire

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).

Source