반응 #72429

반응 방정식

HOBt

triethylamine

H2O

WSC.HCl

Z-Glu-OBzl

H-Nva-OBzl.HCl

→

Z-Glu(Nva-OBzl)-OBzl

용매

methylene chloride

반응 조건

후처리

1. 1
   기타the resulting reaction solution
2. 2
   온도The temperature of the reaction solution was gradually increased
3. 3
   농축Then the reaction solution was concentrated under reduced pressure, ethyl acetate (200 mL)
4. 4
   workup.ADDITIONwas added to the resulting residue
5. 5
   세척the organic phase was then washed once with water (80 mL), twice with a 5% aqueous solution of citric acid (80 mL), once with a saturated common salt solution (80 mL), twice with a 5% aqueous solution of sodium hydrogen carbonate (80 mL)
6. 6
   건조Then, the organic phase was dried over anhydrous magnesium sulfate
7. 7
   기타The magnesium sulfate was removed through filtration
8. 8
   농축the filtrate was concentrated under reduced pressure
9. 9
   기타The resulting residue was recrystallized from ethyl acetate and n-hexane
10. 10
    기타the crystals thus obtained
11. 11
    여과were collected through filtration
12. 12
    기타dried under reduced pressure

실험 절차

The resulting H-Nva-OBzl.HCl was dissolved in methylene chloride (60 mL) and the resulting reaction solution was maintained at 0° C. To the reaction solution, Z-Glu-OBzl (N-α-carbobenzoxy-L-glutamic acid α-benzyl ester, 3.24 g, 8.72 mM), triethylamine (1.34 mL, 1.1 eq., 9.59 mM), HOBt.H2O (1-hydroxybenzotriazole hydrate, 1.47 g, 1.1 eq., 9.59 mM) and WSC.HCl (1.84 g, 1.1 eq., 9.59 mM) were added. The temperature of the reaction solution was gradually increased and stirred at room temperature overnight (16 hours). Then the reaction solution was concentrated under reduced pressure, ethyl acetate (200 mL) was added to the resulting residue, and the organic phase was then washed once with water (80 mL), twice with a 5% aqueous solution of citric acid (80 mL), once with a saturated common salt solution (80 mL), twice with a 5% aqueous solution of sodium hydrogen carbonate (80 mL), and once with a saturated common salt solution (80 mL). Then, the organic phase was dried over anhydrous magnesium sulfate. The magnesium sulfate was removed through filtration and the filtrate was concentrated under reduced pressure. The resulting residue was recrystallized from ethyl acetate and n-hexane, the crystals thus obtained were collected through filtration and dried under reduced pressure to give crystals of Z-Glu(Nva-OBzl)-OBzl (4.05 g).

출처