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

HRID 395942Notes

Reaction equation

HRID 395942 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-8576a9aee98347ed949012ef9a2ddd0c
Source dataset
uspto-grants-2003_08
Patent number
US06605744B2

Reaction notes

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