Gamma-Aminobutyric Acid → 4-Maleimidobutyric Acid
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
Product 1
Reagents, catalysts & solvents 1
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
- concentrationIt is azeotropically concentrated by evaporation
- additionaddition of toluene
- dissolutionthe residue is dissolved in dichloromethane
- custompurified by chromatography on fine silica gel
Sources & evidence
- ORD record
- ord-82e7e49034b94365b8661df093235ec2
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07335775B2
Reaction notes
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