반응 #1479258

반응 방정식

D-2-amino-4-pentenoic acid

triethylamine

water

N-(benzyloxycarbonyloxy)succinimide

→

(2R)-2-{[(benzyloxy)carbonyl]amino}pent-4-enoic acid

용매

Dioxane

반응 조건

후처리

1. 1
   농축concentrated in vacuo
2. 2
   workup.ADDITIONdiluted with saturated NaHCO3
3. 3
   추출extracted with ether (3×)
4. 4
   추출extracted with EtOAc (3×)
5. 5
   세척The combined EtOAc layer was washed with brine
6. 6
   건조dried (Na2SO4)
7. 7
   여과filtered
8. 8
   농축concentrated
9. 9
   기타to give a clear viscous oil (1.17 g, quantitative)

실험 절차

To a suspension of D-2-amino-4-pentenoic acid (500 mg) in Dioxane (20 mL) at RT was added triethylamine (1.09 g), water (0.5 mL), and N-(benzyloxycarbonyloxy)succinimide (2.27 g). The reaction mixture was stirred overnight at RT, concentrated in vacuo, diluted with saturated NaHCO3 and extracted with ether (3×). The basic aqueous layer was acidified to pH 2 with 2N HCl and extracted with EtOAc (3×). The combined EtOAc layer was washed with brine, dried (Na2SO4), filtered and concentrated to give a clear viscous oil (1.17 g, quantitative).

출처