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

HRID 1633804
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HRID 1633804 반응식
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
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참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 3446434Potassium ethyl malonateHCID 5360315Magnesium ChlorideHCID 113120132-[1-(4-Chlorophenyl)ethyl]-4-isopropyl-4-methyl-1,3-oxazol-5-one

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-ab7db74ea7be41cb83ce8ec1b8716500
출처 데이터셋
uspto-grants-2003_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06504046B1

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