Hydrochloric Acid → HCID 11185815, compound

HRID 1633805Notes

Reaction equation

HRID 1633805 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+].[C:21]1([C:27]2[O:28][C:29](=O)[C:30]([CH:33]([CH3:35])[CH3:34])(C)[N:31]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>C(#N)C.O>[CH3:29][C:30]([NH:31][C:27](=[O:28])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([CH:33]([CH3:34])[CH3:35])[C:13](=[O:15])[CH2:12][C:11]([O:17][CH2:18][CH3:19])=[O:16]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 3446434Potassium ethyl malonateHCID 5360315Magnesium ChlorideHCID 10856923HCID 10856923, compound

Product 1

HCID 11185815HCID 11185815, compoundYield 26.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

1.06 g (0.01 mole) of triethylamine and 0.85 g (0.01 mole) of magnesium chloride were added, at room temperature, to a solution of 0.85 g (0.005 mole) of monopotassium ethyl malonate dissolved in 10 ml of acetonitrile, followed by stirring. Thereto was added 1.1 g (0.005 mole) of 2-phenyl-4-isopropyl-4-methyl-1,3-oxazol-5-one. The mixture was stirred at 60° C. for 8 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 0.4 g (0.00131 mole) of ethyl 4,5-dimethyl-3-oxo-4-(benzoylamino)hexanoate (yield=26%).

Workup

  1. stirringThe mixture was stirred at 60° C. for 8 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-beda55261c084a93ad165e3b194fac70
Source dataset
uspto-grants-2003_01
Patent number
US06504046B1

Reaction notes

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