Reaction equation
C(OC(=O)C)(=O)C.[CH3:8][CH:9]([CH2:13][CH2:14][C:15]([OH:17])=O)[C:10](O)=[O:11].[NH4+:18].[OH-]>>[CH3:8][CH:9]1[CH2:13][CH2:14][C:15](=[O:17])[NH:18][C:10]1=[O:11]Participants
Conditions
- Temperature
- 60 °C
Procedure
Acetic anhydride was added to commercially available 2-methylglutaric acid (1 g, 6.8 mmol) at room temperature, and the mixture was stirred at 60° C. for 8 hours under reflux. After completion of the reaction was confirmed by TLC, the remaining acetic anhydride was removed under reduced pressure. The concentrated compound was dissolved in tetrahydrofuran and an ammonia aqueous solution (1.7 mL, 14.6 mmol) was slowly added thereto at 0° C., followed by stirring for 8 hours at room temperature. After the reaction was complete, the remaining ammonia aqueous solution was removed under reduced pressure and an acetic anhydride was added, followed by reflux at 60° C. for 8 hours. The residual acetic anhydride was removed under reduced pressure. The concentrate was purified by column chromatography (ethyl acetate:hexane=1:1) to afford 682 mg (yield: 78%) of the title compound.
Workup
- temperatureunder reflux
- customthe remaining acetic anhydride was removed under reduced pressure
- dissolutionThe concentrated compound was dissolved in tetrahydrofuran
- customat 0° C.
- stirringby stirring for 8 hours at room temperature
- customthe remaining ammonia aqueous solution was removed under reduced pressure
- additionan acetic anhydride was added
- temperatureby reflux at 60° C. for 8 hours
- customThe residual acetic anhydride was removed under reduced pressure
- customThe concentrate was purified by column chromatography (ethyl acetate:hexane=1:1)
Sources & evidence
- ORD record
- ord-31d97895ca8748928ba7fa5a1b3cf919
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08470836B2
Linked notes
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