Acetamidomalonic acid diethyl ester → 1,3-Diethyl 2-(acetylamino)-2-(2-(4-octylphenyl)ethyl)propanedioate

HRID 1795498Notes

Reaction equation

HRID 1795498 reaction equation
[C:1]([NH:4][CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].CC[O-].[Na+].[CH2:20]([C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35]I)=[CH:30][CH:29]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C(O)C.O1CCCC1>[C:1]([NH:4][C:5]([CH2:35][CH2:34][C:31]1[CH:30]=[CH:29][C:28]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:33][CH:32]=1)([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 2723922Sodium ethoxideHCID 105453621-(2-Iodoethyl)-4-octylbenzene

Product 1

HCID 98457531,3-Diethyl 2-(acetylamino)-2-(2-(4-octylphenyl)ethyl)propanedioate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diethyl acetamidomalonate (277 g) and sodium ethylate (86.6 g) in anhydrous ethanol (850 ml) is added a solution of 2-(4-octylphenyl)ethyl iodide (7) (146 g) in anhydrous tetrahydrofuran (533 ml), and the mixture is refluxed under heating for 6 hr. The reaction mixture is concentrated and partitioned between water and hexane, and the hexane layer is washed three times with water. The obtained hexane layer is dried over anhydrous magnesium sulfate and concentrated. The residue is recrystallized from hexane to give the title compound (8) as colorless crystals. The resulting Compound (8) has the same physico-chemical characteristics as indicated in Example 7.

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureunder heating for 6 hr
  3. concentrationThe reaction mixture is concentrated
  4. custompartitioned between water and hexane
  5. washthe hexane layer is washed three times with water
  6. dry with materialThe obtained hexane layer is dried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-c19c091e69a34f1987f2f7d1d7e7957f
Source dataset
uspto-grants-2006_04
Patent number
US07026522B2

Reaction notes

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