HCID 66990889, compound → HCID 58508522, compound

HRID 454668Notes

Reaction equation

HRID 454668 reaction equation
C([O:8][C:9]1[CH:36]=[C:35]([O:37][CH2:38][CH2:39][N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)[CH:34]=[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>CO.C(OCC)(=O)C.[C].[Pd]>[OH:8][C:9]1[CH:36]=[C:35]([O:37][CH2:38][CH2:39][N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)[CH:34]=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:24]=[CH:23][C:15]=1[C:16]([OH:18])=[O:17])=[O:12]

Participants

5

Reactant 1

HCID 66990889HCID 66990889, compound

Product 1

HCID 58508522HCID 58508522, compoundYield 24.5%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution mixture of the obtained tert-butyl 2-(2-(benzyloxy)-4-(2-(morpholin-4-yl)ethoxy)benzamido)-4-phenylbenzoate (0.059 g) in methanol (2.0 mL) and ethyl acetate (2.0 mL), 10% palladium-carbon (0.012 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 3 hours. The insoluble substance was removed by filtration, and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue, and the solid substance was collected by filtration. Trifluoroacetic acid (4.0 mL) was added to the obtained solid substance, followed by stirring at room temperature for 3 hours. Toluene was added to the reaction mixture, and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue, and the solid substance was collected by filtration. Ethanol (4.0 mL) was added to the obtained solid substance. After adjusting the pH to 7.7 with a 1 mol/L aqueous solution of sodium hydroxide, the solid substance was collected by filtration to obtain 0.011 g of 2-(2-hydroxy-4-(2-(morpholin-4-yl)ethoxy)benzamido)-4-phenylbenzoic acid as a white solid.

Workup

  1. additionwas added
  2. customThe insoluble substance was removed by filtration
  3. customthe solvent was evaporated under reduced pressure
  4. additionDiisopropyl ether was added to the obtained residue
  5. filtrationthe solid substance was collected by filtration
  6. additionTrifluoroacetic acid (4.0 mL) was added to the obtained solid substance
  7. stirringby stirring at room temperature for 3 hours
  8. additionToluene was added to the reaction mixture
  9. customthe solvent was evaporated under reduced pressure
  10. additionDiisopropyl ether was added to the obtained residue
  11. filtrationthe solid substance was collected by filtration
  12. additionEthanol (4.0 mL) was added to the obtained solid substance
  13. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-a1d4b476d2d24193bc63d38ebe503610
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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