Hydrochloric Acid → Diethyl acetamido(3-phenylpropyl)propanedioate

HRID 1451571Notes

Reaction equation

HRID 1451571 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].[C:16]1([CH2:22][CH2:23][CH2:24]Br)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>C(O)C>[C:1]([NH:4][C:5]([CH2:24][CH2:23][CH2:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12503(3-Bromopropyl)benzeneHCID 14041Acetamidomalonic acid diethyl ester

Product 1

HCID 21849514Diethyl acetamido(3-phenylpropyl)propanedioate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Sodium (0.23 g) was added to 15 ml of absolute ethanol and the mixture was stirred at room temperature for 30 minutes in a nitrogen flow to give a 10 mmol solution of sodium ethoxide in ethanol. To this solution, 1.98 g of diethyl 2-acetamidomalonate was added and the mixture was heated at 50° C. for 30 minutes in a stream of nitrogen. 3-Phenylpropyl bromide was added thereto at room temperature and the mixture was refluxed under heating for 24 hours. The mixture was neutralized with dilute hydrochloric acid and ethanol was distilled away. The resultant residue was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled away and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4-1:1) and recrystallized from diisopropyl ether-hexane to give 800 mg of diethyl 2-acetamido-2-(3-phenylpropyl)malonate as white crystals.

Workup

  1. temperatureat room temperature and the mixture was refluxed
  2. temperatureunder heating for 24 hours
  3. distillationwas distilled away
  4. extractionThe resultant residue was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled away
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4-1:1)
  9. customrecrystallized from diisopropyl ether-hexane

Sources & evidence

ORD record
ord-b233843f4ef14d9a82784a4b386df2e4
Source dataset
uspto-grants-1997_02
Patent number
US05604229

Reaction notes

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