Gamma-Aminobutyric Acid → 4-Maleimidobutyric Acid

HRID 1247002Notes

Reaction equation

HRID 1247002 reaction equation
[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]

Participants

4

Reactant 2

HCID 119Gamma-Aminobutyric AcidHCID 7923Maleic Anhydride

Product 1

HCID 34049044-Maleimidobutyric AcidYield 48.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6d66671de31e4902ba4832e4028be095
Source dataset
uspto-grants-2006_10
Patent number
US07129254B2

Reaction notes

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