Cesium carbonate → HCID 9912941, compound

HRID 2216291Notes

Reaction equation

HRID 2216291 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

HCID 9912941HCID 9912941, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f80d09f83b1d4414a06ec8dd9f4fd148
Source dataset
uspto-grants-2006_09
Patent number
US07112584B2

Reaction notes

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