반응 #5077

반응 방정식

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

용매

dioxane

반응 조건

후처리

1. 1
   기타prepared by the method of Anderson et al., J
2. 2
   workup.DISSOLUTIONdissolved in a solution
3. 3
   농축Sufficient dry sodium chloride to nearly saturate the solution
4. 4
   workup.ADDITIONwas added
5. 5
   추출The product was extracted into ethyl acetate and it
6. 6
   세척was washed with 0.2N hydrochloric acid
7. 7
   기타prepared in saturated aqueous sodium chloride
8. 8
   건조The organic phase was dried over anhydrous sodium sulfate
9. 9
   여과filtered
10. 10
    기타Solvent was removed by evaporation
11. 11
    기타The product was crystallized from ethyl acetate
12. 12
    기타hexane to yield 7.3 g (mp 86°-89°)

실험 절차

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°).

출처