تفاعل #72429

معادلة التفاعل

HOBt

triethylamine

H2O

WSC.HCl

Z-Glu-OBzl

H-Nva-OBzl.HCl

→

Z-Glu(Nva-OBzl)-OBzl

المذيبات

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   أخرىthe resulting reaction solution
2. 2
   درجة الحرارةThe temperature of the reaction solution was gradually increased
3. 3
   تركيزThen the reaction solution was concentrated under reduced pressure, ethyl acetate (200 mL)
4. 4
   workup.ADDITIONwas added to the resulting residue
5. 5
   غسيلthe 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
   تجفيفThen, the organic phase was dried over anhydrous magnesium sulfate
7. 7
   أخرىThe magnesium sulfate was removed through filtration
8. 8
   تركيزthe filtrate was concentrated under reduced pressure
9. 9
   أخرىThe resulting residue was recrystallized from ethyl acetate and n-hexane
10. 10
    أخرىthe crystals thus obtained
11. 11
    ترشيحwere collected through filtration
12. 12
    أخرىdried under reduced pressure

الإجراء التجريبي

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).

المصدر