Sodium Bicarbonate → ethyl 4-[2-(N-ethoxycarbonyl-N-methylaminomethyl)morpholino]-2,3,5-trifluorobenzoylacetate

HRID 477827

Reaktionsgleichung

Reaktionsgleichung von HRID 477827
[F:1][C:2]1[C:15]([F:16])=[C:14](F)[C:13]([F:18])=[CH:12][C:3]=1[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[CH2:19]([O:21][C:22]([N:24]([CH2:26][CH:27]1[O:32][CH2:31][CH2:30][NH:29][CH2:28]1)[CH3:25])=[O:23])[CH3:20].C(=O)([O-])O.[Na+]>C(#N)C>[CH2:19]([O:21][C:22]([N:24]([CH2:26][CH:27]1[CH2:28][N:29]([C:14]2[C:13]([F:18])=[CH:12][C:3]([C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5])=[C:2]([F:1])[C:15]=2[F:16])[CH2:30][CH2:31][O:32]1)[CH3:25])=[O:23])[CH3:20]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 600916Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoateHCID 146525772-(N-ethoxycarbonyl-N-methylaminomethyl)morpholine

Produkt 1

HCID 14652581ethyl 4-[2-(N-ethoxycarbonyl-N-methylaminomethyl)morpholino]-2,3,5-trifluorobenzoylacetateAusbeute 72,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A suspension of 26.4 g of ethyl 2,3,4,5-tetrafluorobenzoylacetate, 18.7 g of 2-(N-ethoxycarbonyl-N-methylaminomethyl)morpholine and 8.4 g of sodium hydrogen carbonate in 130 ml of acetonitrile is refluxed for 7 hours. The reaction mixture is concentrated under reduced pressure, to the obtained residue is added 100 ml of chloroform and the solution is washed with water. After drying over anhydrous magnesium sulfate, the chloroform is distilled off under reduced pressure and the residue is purified by chromatography on silica gel to give 30.0 g of ethyl 4-[2-(N-ethoxycarbonyl-N-methylaminomethyl)morpholino]-2,3,5-trifluorobenzoylacetate in 67% yield, as an oily substance.

Aufarbeitung

  1. temperatureis refluxed for 7 hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure, to the obtained residue
  3. additionis added 100 ml of chloroform
  4. washthe solution is washed with water
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe chloroform is distilled off under reduced pressure
  7. customthe residue is purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-b97f01db4b1f4bc4a7713f5077875784
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04889857

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