反応 #1479258

反応方程式

D-2-amino-4-pentenoic acid

triethylamine

water

N-(benzyloxycarbonyloxy)succinimide

→

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

溶媒

Dioxane

反応条件

後処理

1. 1
   濃縮concentrated in vacuo
2. 2
   workup.ADDITIONdiluted with saturated NaHCO3
3. 3
   抽出extracted with ether (3×)
4. 4
   抽出extracted with EtOAc (3×)
5. 5
   洗浄The combined EtOAc layer was washed with brine
6. 6
   乾燥dried (Na2SO4)
7. 7
   ろ過filtered
8. 8
   濃縮concentrated
9. 9
   その他to give a clear viscous oil (1.17 g, quantitative)

実験手順

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).

出典