Citric Acid → HCID 57879587, compound

HRID 1673425Notes

Reaction equation

HRID 1673425 reaction equation
I[C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:15]([NH:23][C:24]1[CH:36]=[C:35]([CH:37]=[CH2:38])[CH:34]=[CH:33][C:25]=1[C:26]([O:28]C(C)(C)C)=[O:27])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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:15]([NH:23][C:24]1[CH:36]=[C:35](/[CH:37]=[CH:38]/[C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[CH:3]=2)[CH:34]=[CH:33][C:25]=1[C:26]([OH:28])=[O:27])(=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

8

Reactant 4

HCID 311Citric AcidHCID 10796Cesium carbonateHCID 122723-IodophenolHCID 67343635Tert-butyl 2-(benzamido)-4-vinylbenzoate

Product 1

HCID 57879587HCID 57879587, compoundYield 56.2%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

54 mg of 3-iodophenol, 81 mg of cesium carbonate, 12 mg of tetrabutylammonium bromide and 19 mg of polymer supported bis(acetato)triphenylphosphine palladium(II) were added to 1.0 mL of toluene solution containing 40 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, 19 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; 40-90% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to obtain 25 mg of 2-(benzamido)-4-((E)-2-(3-hydroxyphenyl)vinyl)benzoic acid as white solid.

Workup

  1. additionwas added
  2. stirringstirred at 110° C. for 24 hours
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. washafter washed with 10% citric acid aqueous solution
  7. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  8. addition10 mL of trifluoroacetic acid was added to the obtained residue
  9. stirringstirred at room temperature for 1 hour
  10. customThe solvent was evaporated under reduced pressure
  11. customthe obtained residue was purified with reversed-phase silica gel column chromatography [eluent; 40-90% acetonitrile/0.1% trifluoroacetic acid aqueous solution]

Sources & evidence

ORD record
ord-29cc44d8c1f04a459257bfee7b91c315
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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