تفاعل #5077

معادلة التفاعل

N-hydroxy-succinimide

Ac-Ala-OH

H-Lys(Boc)-OH

H-Lys(Boc)-OH

sodium hydroxide

hydrochloric acid

Ac-Ala-OH

triethylamine

→

Ac-Ala-Lys(Boc)-OH

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   أخرىprepared by the method of Anderson et al., J
2. 2
   workup.DISSOLUTIONdissolved in a solution
3. 3
   تركيزSufficient dry sodium chloride to nearly saturate the solution
4. 4
   workup.ADDITIONwas added
5. 5
   استخلاصThe product was extracted into ethyl acetate and it
6. 6
   غسيلwas washed with 0.2N hydrochloric acid
7. 7
   أخرىprepared in saturated aqueous sodium chloride
8. 8
   تجفيفThe organic phase was dried over anhydrous sodium sulfate
9. 9
   ترشيحfiltered
10. 10
    أخرىSolvent was removed by evaporation
11. 11
    أخرىThe product was crystallized from ethyl acetate
12. 12
    أخرىhexane to yield 7.3 g (mp 86°-89°)

الإجراء التجريبي

Ac-Ala-Lys(Boc)-OH was prepared by coupling the N-hydroxysuccinimide ester of Ac-Ala-OH, prepared by the method of Anderson et al., J. Am. Chem. Soc. 86: 1839, (1964), to H-Lys(Boc)-OH. The N-hydroxy-succinimide of Ac-Ala-OH (6.25 g, 27.4 mmoles) was dissolved in 30 mL of dioxane and was added to a solution of H-Lys(Boc)-OH (7.50 g, 30.4 mmoles) dissolved in a solution consisting of 30 mL of 1.0N sodium hydroxide and triethylamine (2.12 mL, 15.0 mmoles). The reaction mixture was stirred overnight, then acidified with hydrochloric acid. Sufficient dry sodium chloride to nearly saturate the solution was added. The product was extracted into ethyl acetate and it was washed with 0.2N hydrochloric acid prepared in saturated aqueous sodium chloride. The organic phase was dried over anhydrous sodium sulfate and filtered. Solvent was removed by evaporation. The product was crystallized from ethyl acetate:hexane to yield 7.3 g (mp 86°-89°).

المصدر