Cesium carbonate → HCID 15463547, compound

HRID 430470Notes

Reaction equation

HRID 430470 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([CH2:12][C:13](=[O:27])[C:14]([NH:16][C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[C:22](=[O:23])[O:21][CH2:20]3)=[O:15])[CH2:11][CH2:10]1.[F:28][C:29]([Si](C)(C)C)([F:31])[F:30].C(=O)([O-])[O-].[Cs+].[Cs+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O.O1CCCC1.O>[OH:27][C:13]([C:29]([F:31])([F:30])[F:28])([CH2:12][C:9]1([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH2:10][CH2:11]1)[C:14]([NH:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[C:22](=[O:23])[O:21][CH2:20]2)=[O:15]

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 18350646HCID 18350646, compound

Product 1

HCID 15463547HCID 15463547, compound

Reagents, catalysts & solvents 4

HCID 962WaterCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

500 mg of 5-{3-[1-(2-methoxyphenyl)-cyclopropyl]-2-oxo-propionylamino}-phthalide is dissolved under argon in 15 ml of dimethylformamide and mixed with 0.77 ml of trifluoromethyl-trimethylsilane and 500 mg of cesium carbonate while being cooled with ice. After 18 hours of stirring at room temperature, 5 ml of a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran and a few drops of water are added and stirred for one hour at room temperature. After 100 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), the title compound is obtained in a pure state.

Workup

  1. temperaturewhile being cooled with ice
  2. stirringstirred 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-3e4567bce6df4ce1886f17aa817cbe8c
Source dataset
uspto-grants-2001_11
Patent number
US06323199B1

Reaction notes

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