Cesium carbonate → HCID 9912941, Verbindung

HRID 2216291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2216291
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([CH3:30])([CH3:29])[CH2:11][C:12](=[O:28])[C:13]([NH:15][C:16]3[CH:17]=[CH:18][C:19]4[C:24](=[O:25])[O:23][N:22]=[C:21]([CH3:26])[C:20]=4[CH:27]=3)=[O:14])[C:4]=2[O:3][CH2:2]1.[F:31][C:32]([Si](C)(C)C)([F:34])[F:33].C(=O)([O-])[O-].[Cs+].[Cs+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([CH3:30])([CH3:29])[CH2:11][C:12]([OH:28])([C:32]([F:34])([F:33])[F:31])[C:13]([NH:15][C:16]3[CH:17]=[CH:18][C:19]4[C:24](=[O:25])[O:23][N:22]=[C:21]([CH3:26])[C:20]=4[CH:27]=3)=[O:14])[C:4]=2[O:3][CH2:2]1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 12148502HCID 12148502, Verbindung

Produkt 1

HCID 9912941HCID 9912941, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2.67 g of 6-[4-(benzo[1,3]dioxol-4-yl)-4-methyl-2-oxo-valeroyl-amino]-4-methyl-2,3-benzoxazin-1-one is dissolved under argon in 35 ml of dimethylformamide and mixed with 4.66 ml of trifluoromethyl-trimethylsilane and 2.6 g of cesium carbonate while being cooled with ice. After 18 hours of stirring at room temperature, a spatula tip full of tetrabutylammonium fluoride is added, and it is stirred for one hour at room temperature. After 300 ml of water is added, it is extracted with ethyl acetate, the organic phase is dried (Na2SO4) and concentrated by evaporation. The crude product is chromatographed on silica gel. With hexane/ethyl acetate (80:20), 1.33 g of the title compound is obtained in a pure state.

Aufarbeitung

  1. temperaturewhile being cooled with ice
  2. stirringit is stirred for one hour at room temperature
  3. extractionit is extracted with ethyl acetate
  4. dry with materialthe organic phase is dried (Na2SO4)
  5. concentrationconcentrated by evaporation
  6. customThe crude product is chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f80d09f83b1d4414a06ec8dd9f4fd148
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07112584B2

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