Reaction equation
[O-]CC.[Na+].[C:5]([NH:8][CH:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:7])[CH3:6].Cl[CH2:21][C:22]1[C:23]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:24]([O:28][CH3:29])[CH:25]=[CH:26][CH:27]=1.O>C(O)C.C(O)(=O)C>[C:5]([NH:8][C:9]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[C:23]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:7])[CH3:6]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A quantity of 136.20 g (0.42 mole) of 21 wt.% sodium ethoxide in ethanol is added to a stirred solution of 90.14 g (0.415 mole) of diethyl acetamidomalonate (Aldrich) in 800 mL of absolute ethanol. A solution of the benzyl chloride derivative of Example 38 in 500 mL of absolute ethanol is added and the mixture is heated at reflux for 2 hours. The cooled mixture is poured into 4 L of ice and water containing 20.0 g of glacial acetic acid. The supernatant is decanted from the separated gum. The gum is dissolved in 2 L of ether, the solution dried (magnesium sulfate), and concentrated to ca 300 mL volume. Petroleum ether (100 mL) is added to precipitate 107.1 g (66.4% yield) of pure crystalline product; mp 94°-96° C.
Workup
- temperaturethe mixture is heated
- temperatureat reflux for 2 hours
- customThe supernatant is decanted from the separated gum
- dissolutionThe gum is dissolved in 2 L of ether
- dry with materialthe solution dried (magnesium sulfate)
- concentrationconcentrated to ca 300 mL volume
Sources & evidence
- ORD record
- ord-f93f0562c268458cb7f1687b9cb17055
- Source dataset
- uspto-grants-1993_09
- Patent number
- US05246943
Linked notes
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