Diisopropylcarbodiimide → N-[5-(4-fluoro-phenyl)-isoxazol-3-yl]-malonamic acid ethyl ester

HRID 1665687Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1665687
C(N=C=NC(C)C)(C)C.[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:21][N:20]=[C:19]([NH2:22])[CH:18]=2)=[CH:13][CH:12]=1.[CH2:23]([O:25][C:26](=[O:31])[CH2:27][C:28](O)=[O:29])[CH3:24]>C1COCC1.C(OCC)(=O)C>[CH2:23]([O:25][C:26](=[O:31])[CH2:27][C:28]([NH:22][C:19]1[CH:18]=[C:17]([C:14]2[CH:13]=[CH:12][C:11]([F:10])=[CH:16][CH:15]=2)[O:21][N:20]=1)=[O:29])[CH3:24]

Komponenten

6

Edukt 3

HCID 12734DiisopropylcarbodiimideHCID 70615Monoethyl malonateHCID 132004245-(4-Fluorophenyl)-1,2-oxazol-3-amine

Produkt 1

HCID 57875802N-[5-(4-fluoro-phenyl)-isoxazol-3-yl]-malonamic acid ethyl esterAusbeute 832,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Diisopropyl carbodiimide (0.07 mL, 0.45 mmol) and 5-(4-fluoro-phenyl)-isoxazol-3-ylamine (67 mg, 0.037 mmol) were added to a stirred solution of malonic acid monoethyl ester (50 mg, 0.37 mmol) in THF (1 mL) and stirring was continued at reflux temperature for 4 hrs. The mixture was concentrated under reduced pressure. The residue obtained was diluted with ethyl acetate and washed with water, followed by brine solution. The organic layer collected was dried over Na2SO4 and concentrated under reduced pressure to afford 90 mg (81.8% Yield) of N-[5-(4-fluoro-phenyl)-isoxazol-3-yl]-malonamic acid ethyl ester.

Aufarbeitung

  1. temperatureat reflux temperature for 4 hrs
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customThe residue obtained
  4. washwashed with water
  5. customThe organic layer collected
  6. dry with materialwas dried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bc9c2154121c46a0bc19592d5d1bb707
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039463B2

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