Hydrochloric Acid → Ac-Ala-Lys(Boc)-OH

HRID 4981

Reaktionsgleichung

Reaktionsgleichung von HRID 4981
[NH:1]([C:7]([CH3:9])=[O:8])[C@H:2]([C:4](O)=[O:5])[CH3:3].[NH2:10][C@H:11]([C:24]([OH:26])=[O:25])[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].ON1C(=O)CCC1=O.[OH-].[Na+].C(N(CC)CC)C.Cl>O1CCOCC1>[NH:1]([C:7]([CH3:9])=[O:8])[C@H:2]([C:4]([NH:10][C@H:11]([C:24]([OH:26])=[O:25])[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])=[O:5])[CH3:3]

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 80170N-HydroxysuccinimideHCID 88064N-Acetyl-L-alanine2×HCID 2733283(2S)-2-amino-6-(((tert-butoxy)carbonyl)amino)hexanoic acid2×

Produkt 1

HCID 131717743Ac-Ala-Lys(Boc)-OH

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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°).

Aufarbeitung

  1. customprepared by the method of Anderson et al., J
  2. dissolutiondissolved in a solution
  3. concentrationSufficient dry sodium chloride to nearly saturate the solution
  4. additionwas added
  5. extractionThe product was extracted into ethyl acetate and it
  6. washwas washed with 0.2N hydrochloric acid
  7. customprepared in saturated aqueous sodium chloride
  8. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customSolvent was removed by evaporation
  11. customThe product was crystallized from ethyl acetate
  12. customhexane to yield 7.3 g (mp 86°-89°)

Quellen und Nachweise

ORD-Eintrag
ord-408c8484fe124834b5520e846e9adf68
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242904

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