Potassium Hydroxide → Boc-D-Glu-OH

HRID 2187351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2187351
[NH2:1][C@@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[OH:6].[OH-].[K+].[O:13](C(OC(C)(C)C)=O)[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=O>O.O1CCOCC1>[NH:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:13])[C@@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:6])[OH:7]

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 23327D-Glutamic AcidHCID 90495Di-tert-butyl dicarbonate

Produkt 1

HCID 7019046Boc-D-Glu-OH

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

14.7 g (0.1 Mol) of H-D-Glu-OH was dissolved in 200 ml of distilled water, and the pH was adjusted to 10.2 with 0.1 M potassium hydroxide. 33.0 g (0.3 Mol) of BOC2O in dioxane was added with intensive mixing. The pH was controlled using a pH-stat. After completion of the reaction, the mixture was transferred to a separating funnel, and extraction was carried out from the alkaline solution with ethyl acetate (3×150 ml). The pH of the aqueous phase was adjusted to 3.0 using 0.2% sulphuric acid, and Boc-D-Glu-OH was extracted from the organic phase (3×200 ml). The organic phase was washed three times with 200 ml of Na2SO4 saturated solution to neutral pH, and dried over Na2SO4, and evaporated to oil under vacuum. The yield was 16.7 g (68%).

Aufarbeitung

  1. customAfter completion of the reaction
  2. customthe mixture was transferred to a separating funnel
  3. extractionextraction
  4. extractionwas extracted from the organic phase (3×200 ml)
  5. washThe organic phase was washed three times with 200 ml of Na2SO4 saturated solution to neutral pH
  6. dry with materialdried over Na2SO4
  7. customevaporated to oil under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-88fcbbd65a6841daa308f2a4059b7d9a
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06410515B1

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