Hydrochloric Acid → Ethyl 4-[2-(4-chlorophenyl)propanoylamino]-4,5-dimethyl-3-oxohexanoate

HRID 1633804Notes

Reaction equation

HRID 1633804 reaction equation
C(N(CC)CC)C.[Cl-].[Mg+2].[Cl-].[C:11]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:12][C:13]([O-:15])=O.[K+].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([C:30]2[O:31][C:32](=O)[C:33]([CH:36]([CH3:38])[CH3:37])(C)[N:34]=2)[CH3:29])=[CH:24][CH:23]=1.Cl>O.C(#N)C>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([CH:28]([CH3:29])[C:30]([NH:34][C:33]([CH3:32])([CH:36]([CH3:38])[CH3:37])[C:13](=[O:15])[CH2:12][C:11]([O:17][CH2:18][CH3:19])=[O:16])=[O:31])=[CH:26][CH:27]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 3446434Potassium ethyl malonateHCID 5360315Magnesium ChlorideHCID 11312013HCID 11312013, compound

Product 1

HCID 18680197Ethyl 4-[2-(4-chlorophenyl)propanoylamino]-4,5-dimethyl-3-oxohexanoateYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

0.73 g (0.00722 mole) of triethylamine and 0.41 g (0.0043 mole) of magnesium chloride were added, at room temperature, to a solution of 0.73 g (0.0043 mole) of monopotassium ethyl malonate dissolved in :10 ml of acetonitrile, followed by stirring. Thereto was added 0.8 g (0.00287 mole) of 2-[1-(4-chlorophenyl)ethyl]-4-isopropyl-4-methyl-1,3-oxazol-5-one. The mixture was stirred at 60° C. for 5 hours to give rise to a reaction. After the completion of the reaction, the reaction mixture was cooled. Thereto were added 50 ml of water and diluted hydrochloric acid to adjust the mixture to a pH of 4 or less. The mixture was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate, and concentrated. The concentrate was subjected to separation by column chromatography to obtain 0.5 g (0.00136 mole) of ethyl 4-[2-(4-chlorophenyl)propanoylamino]-4,5-dimethyl-3-oxohexanoate (yield=48%).

Workup

  1. stirringThe mixture was stirred at 60° C. for 5 hours
  2. customto give rise
  3. customto a reaction
  4. customAfter the completion of the reaction
  5. temperaturethe reaction mixture was cooled
  6. extractionThe mixture was subjected to extraction with ethyl acetate
  7. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution
  8. dry with materiala saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customThe concentrate was subjected to separation by column chromatography

Sources & evidence

ORD record
ord-ab7db74ea7be41cb83ce8ec1b8716500
Source dataset
uspto-grants-2003_01
Patent number
US06504046B1

Reaction notes

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