Citric Acid → HCID 57879400, compound

HRID 1673427Notes

Reaction equation

HRID 1673427 reaction equation
[CH:1]1[O:2][CH:3]=[CH:4][C:5]2[C:6]=1[CH:7]=[CH:8][CH:9]=2.C(=O)([O-])[O-].[Cs+].[Cs+].[C:16]([NH:24][C:25]1[CH:37]=[C:36]([CH:38]=[CH2:39])[CH:35]=[CH:34][C:26]=1[C:27]([O:29]C(C)(C)C)=[O:28])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:16]([NH:24][C:25]1[CH:37]=[C:36](/[CH:38]=[CH:39]/[C:9]2[CH:5]=[CH:4][C:3]3[O:2][CH:1]=[CH:6][C:7]=3[CH:8]=2)[CH:35]=[CH:34][C:26]=1[C:27]([OH:29])=[O:28])(=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 311Citric AcidHCID 10796Cesium carbonateHCID 14144377HCID 14144377, compoundHCID 67343635Tert-butyl 2-(benzamido)-4-vinylbenzoate

Product 1

HCID 57879400HCID 57879400, compoundYield 4%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

61 mg of 5-benzofuran, 0.10 g of cesium carbonate, 15 mg of tetrabutylammonium bromide and 21 mg of polymer supported bis(acetato)triphenylphosphine palladium(II) were added to 1.0 mL of toluene solution containing 50 mg of tert-butyl 2-(benzamido)-4-vinylbenzoate at room temperature and stirred at 110° C. for 24 hours. After the reaction mixture was cooled to room temperature, 24 mg of polymer supported bis(acetato)triphenylphosphine palladium(II) was added and stirred at 110° C. for 24 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 10% citric acid aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. 10 mL of trifluoroacetic acid was added to the obtained residue and stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure and the obtained residue was purified with reversed-phase silica gel column chromatography [eluent; 60-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to obtain 2.4 mg of 2-(benzamido)-4-((E)-2-(benzofuran-5-yl)vinyl)benzoic acid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. additionwas added
  3. stirringstirred at 110° C. for 24 hours
  4. temperatureAfter the reaction mixture was cooled to room temperature
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. washafter washed with 10% citric acid aqueous solution
  8. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  9. addition10 mL of trifluoroacetic acid was added to the obtained residue
  10. stirringstirred at room temperature for 1 hour
  11. customThe solvent was evaporated under reduced pressure
  12. customthe obtained residue was purified with reversed-phase silica gel column chromatography [eluent; 60-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution]

Sources & evidence

ORD record
ord-88b5b54334ac4fcb86687ac48f0f5cb9
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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