Acetic Acid → HCID 58508898, compound

HRID 454540Notes

Reaction equation

HRID 454540 reaction equation
C([O:8][C:9]1[CH:36]=[CH:35][C:34]([C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:23][C:15]=1[C:16]([O:18]C(C)(C)C)=[O:17])=[O:12])C1C=CC=CC=1.C(O)(=O)C>C(OCC)(=O)C.CO.[C].[Pd]>[OH:8][C:9]1[CH:36]=[CH:35][C:34]([C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:23][C:15]=1[C:16]([OH:18])=[O:17])=[O:12]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 66990202HCID 66990202, compound

Product 1

HCID 58508898HCID 58508898, compoundYield 67.8%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalyst3×HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution mixture of the obtained tert-butyl 2-(2-(benzyloxy)-5-(pyridin-3-yl)benzamido)-4-phenylbenzoate (0.14 g) in ethyl acetate (1 mL) and methanol (1 mL), 10% palladium-carbon (14 mg) was added, followed by stirring under a hydrogen atmosphere at room temperature for 1 hour and 30 minutes. To the reaction mixture, 10% palladium-carbon (14 mg) was added. The resulting mixture was stirred under a hydrogen atmosphere at room temperature for 2 hours and 30 minutes. Acetic acid (2 mL) and 10% palladium-carbon (0.11 g) were added to the reaction mixture, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours. The insoluble substance was removed by filtration, and the solvent was evaporated under reduced pressure. Ethyl acetate and a saturated aqueous solution of sodium bicarbonate were added to the residue. The organic layer was separated, washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Trifluoroacetic acid (5 mL) was added to the obtained residue, followed by stirring at room temperature for 5 hours. The solvent was evaporated under reduced pressure, and water and ethyl acetate were added to the residue. After adjusting the pH to 5 with a saturated aqueous solution of sodium bicarbonate, the solid substance was collected by filtration to obtain 0.070 g of 2-(2-hydroxy-5-(pyridin-3-yl)benzamido)-4-phenylbenzoic acid as a white solid.

Workup

  1. additionwas added
  2. stirringThe resulting mixture was stirred under a hydrogen atmosphere at room temperature for 2 hours and 30 minutes
  3. stirringby stirring under a hydrogen atmosphere at room temperature for 2 hours
  4. customThe insoluble substance was removed by filtration
  5. customthe solvent was evaporated under reduced pressure
  6. additionEthyl acetate and a saturated aqueous solution of sodium bicarbonate were added to the residue
  7. customThe organic layer was separated
  8. washwashed with a saturated aqueous solution of sodium bicarbonate
  9. dry with materiala saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. additionTrifluoroacetic acid (5 mL) was added to the obtained residue
  12. stirringby stirring at room temperature for 5 hours
  13. customThe solvent was evaporated under reduced pressure, and water and ethyl acetate
  14. additionwere added to the residue
  15. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-40fb606cb4c74a708ebc7b43845fa864
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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