Potassium Carbonate → (+/-)-Ethyl 2-ethoxy-3-[4-[2-[2,2dimethyl4-oxo-3,4-dihydro-1,3-benzoxazin-3-yl]ethoxy]phenyl]propanoate

HRID 432980

Reaktionsgleichung

Reaktionsgleichung von HRID 432980
[CH3:1][C:2]1([CH3:13])[NH:7][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[O:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:20]([O:22][CH:23]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38]Br)=[CH:32][CH:31]=1)[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:21]>CN(C=O)C.O>[CH2:20]([O:22][CH:23]([CH2:29][C:30]1[CH:31]=[CH:32][C:33]([O:36][CH2:37][CH2:38][N:7]2[C:6](=[O:8])[C:5]3[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=3[O:3][C:2]2([CH3:13])[CH3:1])=[CH:34][CH:35]=1)[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:21]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 7174282,2-dimethyl-3,4-dihydro-2H-1,3-benzoxazin-4-oneHCID 11002461Ethyl 2-ethoxy-3-[4-(2-bromoethoxy)-phenyl]propanoate

Produkt 1

HCID 18760899(+/-)-Ethyl 2-ethoxy-3-[4-[2-[2,2dimethyl4-oxo-3,4-dihydro-1,3-benzoxazin-3-yl]ethoxy]phenyl]propanoateAusbeute 45,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 2,2-dimethyl-4-oxo-3,4-dihydro-1,3-benzoxazine (0.3 g, 1.69 mmol) in DMF (3 mL) was added potassium carbonate (0.47 g, 3.39 mmol) and stirred for 30 min. To this reaction mixture was added a solution of ethyl 2-ethoxy-3-[4-(2-bromoethoxy) phenyl]propanoate (0.70 g, 2.03 mmol) (disclosed in U.S. patent application Ser. No. 09/012,585) in DMF (1 mL) and stirred for 24 h at 60-70° C. The reaction mixture was diluted with water and extracted with ethyl acetate (3×10 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was chromatographed on silica gel using a gradient of 5-15% of ethyl acetate in pet ether as eluent to afford the title compound (0.34 g, 45%) as a liquid.

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel using a gradient of 5-15% of ethyl acetate in pet ether as eluent

Quellen und Nachweise

ORD-Eintrag
ord-46a29ca1873e4f0eba591faa887f6cdb
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06664411B2

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