Acetic Acid → 2-Acetylamino-5-(3-ethylphenyl)-3-oxo-pentanoic acid, ethyl ester
Reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11](=[O:20])[C:12](=[N:18]O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=[CH:7][CH:8]=1)[CH3:2].O.[C:22](O)(=[O:24])[CH3:23]>C(OC(=O)C)(=O)C.[Zn]>[C:22]([NH:18][CH:12]([C:11](=[O:20])[CH2:10][CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[CH:4]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:24])[CH3:23]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
To a stirred solution of the product from step (iv) (20.9 g) in acetic acid (100 ml) and acetic anhydride (25 ml) was added zinc dust (30 g) portionwise at a rate to maintain the internal temperature <40° C. The mixture was stirred for 18 hours and water (125 ml) was added at such a rate as to maintain the temperature at around 40° C. The mixture was stirred at room temperature for 1 hour and filtered. The filtrate was extracted with dichloromethane and the extract was washed with water and saturated aqueous sodium bicarbonate solution. The organic phase was collected, dried (MgSO4) and evaporated under reduced pressure to give a yellow oil.
Workup
- temperatureto maintain the internal temperature <40° C
- stirringThe mixture was stirred at room temperature for 1 hour
- filtrationfiltered
- extractionThe filtrate was extracted with dichloromethane
- washthe extract was washed with water and saturated aqueous sodium bicarbonate solution
- customThe organic phase was collected
- dry with materialdried (MgSO4)
- customevaporated under reduced pressure
- customto give a yellow oil
Sources & evidence
- ORD record
- ord-c411c992fe764704be7a4ccf577a93d0
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06218376B1
Reaction notes
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