Water → HCID 12148502, Verbindung

HRID 2216290Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2216290
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([CH3:18])([CH3:17])[CH2:11][C:12](=[O:16])[C:13]([OH:15])=O)[C:4]=2[O:3][CH2:2]1.S(Cl)(Cl)=O.[NH2:23][C:24]1[CH:25]=[CH:26][C:27]2[C:32](=[O:33])[O:31][N:30]=[C:29]([CH2:34]C)[C:28]=2[CH:36]=1.O>CC(N(C)C)=O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([CH3:18])([CH3:17])[CH2:11][C:12](=[O:16])[C:13]([NH:23][C:24]3[CH:25]=[CH:26][C:27]4[C:32](=[O:33])[O:31][N:30]=[C:29]([CH3:34])[C:28]=4[CH:36]=3)=[O:15])[C:4]=2[O:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 21941648HCID 21941648, VerbindungHCID 21941653HCID 21941653, Verbindung

Produkt 1

HCID 12148502HCID 12148502, VerbindungAusbeute 40,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

10 g of 4-(benzo[1,3]dioxol-4-yl)-4-methyl-2-oxo-pentanoic acid is dissolved in 125 ml of dimethylacetamide and mixed with 3.5 ml of thionyl chloride under argon at −0° C. After 20 minutes of stirring at −3 to +3° C., 7.6 g of 6-amino-4-ethyl-2,3-benzoxazin-1-one (WO00/32584) is added. It is stirred for 96 hours at room temperature, then mixed with water, extracted with ethyl acetate, the organic phase is washed with water, dried (Na2SO4), and after the solvent is concentrated by evaporation and after chromatography of the crude product on silica gel with hexane/ethyl acetate (100:0→60:40), 6.56 g of 6-[4-(benzo[1,3]dioxol-4-yl)-4-methyl-2-oxo-valeroyl-amino]-4-methyl-2,3-benzoxazin-1-one is obtained as a beige solid.

Aufarbeitung

  1. stirringIt is stirred for 96 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washthe organic phase is washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationafter the solvent is concentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-9a6f0036930c49c79c0dc72d8577c5e4
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07112584B2

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