Cesium carbonate → HCID 21902076, compound

HRID 1160334Notes

Reaction equation

HRID 1160334 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([N:14]3[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20][O:21]S(C)(=O)=O)[CH2:15]3)=[O:13])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:26]1[O:30][C:29]2[CH:31]=[C:32](O)[CH:33]=[CH:34][C:28]=2[O:27]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[O:27]1[C:28]2[CH:34]=[CH:33][C:32]([O:21][CH2:20][CH:16]3[CH2:17][CH2:18][CH2:19][N:14]([C:12]([C:8]4([C:5]5[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=5)[CH2:11][CH2:10][CH2:9]4)=[O:13])[CH2:15]3)=[CH:31][C:29]=2[O:30][CH2:26]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 68289SesamolHCID 12992442Methanesulfonic acid 1-[1-(4-chloro-phenyl)-cyclobutanecarbonyl]-piperidin-3-ylmethyl ester

Product 1

HCID 21902076HCID 21902076, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 43 (1.0 g, 2.59 mmol) in acetonitrile (25 mL) was added sesamol (0.36 g, 2.59 mmol) and cesium carbonate (1.27 g, 3.89 mmol). The reaction was stirred and refluxed for 20 h. After cooling to room temperature, the reaction mixture was filtered and most of the solvent was removed by rotary evaporation. The residue was partitioned between dichloromethane and water, and the organic layer was washed with sat. sodium carbonate (2×50 mL) and water. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated by rotary evaporation. The residue was purified by chromatography on silica gel, eluting with dichloromethane/methanol (98:2) to give 0.68 g of the amide 44 as a crystalline solid. C24H26ClNO4, MS (m/z)=428 (MH+).

Workup

  1. temperaturerefluxed for 20 h
  2. filtrationthe reaction mixture was filtered and most of the solvent
  3. customwas removed by rotary evaporation
  4. customThe residue was partitioned between dichloromethane and water
  5. washthe organic layer was washed with sat. sodium carbonate (2×50 mL) and water
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. customThe residue was purified by chromatography on silica gel
  10. washeluting with dichloromethane/methanol (98:2)

Sources & evidence

ORD record
ord-edc639c0f049480086e320e2c20d83ed
Source dataset
uspto-grants-2010_10
Patent number
US07816375B2

Reaction notes

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