Gamma-Aminobutyric Acid → 4-Maleimidobutyric Acid

HRID 1247002Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1247002
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[C:8]1(=O)[O:13][C:11](=[O:12])[CH:10]=[CH:9]1>C(O)(=O)C>[O:12]=[C:11]1[CH:10]=[CH:9][C:8](=[O:13])[N:1]1[CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6]

Komponenten

4

Edukt 2

HCID 119Gamma-Aminobutyric AcidHCID 7923Maleic Anhydride

Produkt 1

HCID 34049044-Maleimidobutyric AcidAusbeute 48,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

20.0 g (193.9 mmol) of 4-aminobutyric acid is mixed with 19 g of maleic acid anhydride, 290 ml of acetic acid, and it is heated for 4 hours in an oil bath at 130° C. It is azeotropically concentrated by evaporation with repeated addition of toluene, the residue is dissolved in dichloromethane and purified by chromatography on fine silica gel. 17.1 g (93.4 mmol, 48%) of the title compound is isolated as a crystalline solid.

Aufarbeitung

  1. concentrationIt is azeotropically concentrated by evaporation
  2. additionaddition of toluene
  3. dissolutionthe residue is dissolved in dichloromethane
  4. custompurified by chromatography on fine silica gel

Quellen und Nachweise

ORD-Eintrag
ord-6d66671de31e4902ba4832e4028be095
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129254B2

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