Beta-Alanine → 3-Maleimidopropionic acid
Reaction equation
[C:1]1(=[O:7])[O:6][C:4](=O)[CH:3]=[CH:2]1.[NH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12].C1(C)C=CC=CC=1>C(O)(=O)C>[C:11]([CH2:10][CH2:9][N:8]1[C:1](=[O:7])[CH:2]=[CH:3][C:4]1=[O:6])([OH:13])=[O:12]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
To a solution of maleic anhydride (33.6 g, 377 mmol) and β-alanine (36.96 g, 377 mmol) in 400 mL of acetic acid was added 52 mL toluene, the mixture was an opaque suspension. Heating to 140° C. provided a clear solution, which was refluxed for 5 hours. To the solution was added 50 mL toluene and reflux was continued. In the next 4 hours 31 mL acetic acid/water mixture was separated by distillation using a Dean-Stark apparatus. The reaction mixture was cooled to 90° C. and solvent was removed via distillation with water aspiration. The residue viscous oil was taken up in 200 mL acetone and concentrated. The crude product was purified through a flash chromatography on silica gel with a gradient eluent of 5-12% methanol in dichloromethane to afford 35 g of 1 as white solid. 1H NMR (CDCl3) δ 6.70 (s, 2H), 3.81 (t, 7.2 Hz, 2H), 2.68 (t, 7.2 Hz, 2H), 2.14 (s, 1H).
Workup
- customprovided a clear solution, which
- temperaturewas refluxed for 5 hours
- temperaturereflux
- customIn the next 4 hours 31 mL acetic acid/water mixture was separated by distillation
- temperatureThe reaction mixture was cooled to 90° C.
- customsolvent was removed via distillation with water aspiration
- concentrationconcentrated
- customThe crude product was purified through a flash chromatography on silica gel with a gradient eluent of 5-12% methanol in dichloromethane
Sources & evidence
- ORD record
- ord-41b465bd580c4452ae34b3326121d4a1
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07346259B1
Reaction notes
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