Réaction #72429

Équation de réaction

HOBt

triethylamine

H2O

WSC.HCl

Z-Glu-OBzl

H-Nva-OBzl.HCl

→

Z-Glu(Nva-OBzl)-OBzl

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   Autrethe resulting reaction solution
2. 2
   TempératureThe temperature of the reaction solution was gradually increased
3. 3
   ConcentrationThen the reaction solution was concentrated under reduced pressure, ethyl acetate (200 mL)
4. 4
   workup.ADDITIONwas added to the resulting residue
5. 5
   Lavagethe 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
   SéchageThen, the organic phase was dried over anhydrous magnesium sulfate
7. 7
   AutreThe magnesium sulfate was removed through filtration
8. 8
   Concentrationthe filtrate was concentrated under reduced pressure
9. 9
   AutreThe resulting residue was recrystallized from ethyl acetate and n-hexane
10. 10
    Autrethe crystals thus obtained
11. 11
    Filtrationwere collected through filtration
12. 12
    Autredried under reduced pressure

Mode opératoire

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).

Source