Tert-butyl 2-(2-(benzyloxy)-5-phenoxybenzamido)-4-phenylbenzoate → Tert-butyl 2-(2-hydroxy-5-phenoxybenzamido)-4-phenylbenzoate

HRID 454633Notes

Reaction equation

HRID 454633 reaction equation
C([O:8][C:9]1[CH:36]=[CH:35][C:34]([O:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=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:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:12])C1C=CC=CC=1>CO.C(OCC)(=O)C.[C].[Pd]>[OH:8][C:9]1[CH:36]=[CH:35][C:34]([O:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=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:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:12]

Participants

5

Reactant 1

HCID 66991357Tert-butyl 2-(2-(benzyloxy)-5-phenoxybenzamido)-4-phenylbenzoate

Product 1

HCID 58508591Tert-butyl 2-(2-hydroxy-5-phenoxybenzamido)-4-phenylbenzoateYield 41.2%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution mixture of the obtained tert-butyl 2-(2-(benzyloxy)-5-phenoxybenzamido)-4-phenylbenzoate (0.049 g) in methanol (1.5 mL) and ethyl acetate (1.5 mL), 10% palladium-carbon (0.025 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours. To the reaction mixture, 10% palladium-carbon (0.050 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours. Ethyl acetate was added to the reaction mixture, and the insoluble substance was removed by filtration. The solvent was evaporated under reduced pressure, and hexane was added to the obtained residue. The solid substance was collected by filtration to obtain 0.017 g of tert-butyl 2-(2-hydroxy-5-phenoxybenzamido)-4-phenylbenzoate as a white solid.

Workup

  1. additionwas added
  2. stirringby stirring under a hydrogen atmosphere at room temperature for 2 hours
  3. customthe insoluble substance was removed by filtration
  4. customThe solvent was evaporated under reduced pressure, and hexane
  5. additionwas added to the obtained residue
  6. filtrationThe solid substance was collected by filtration

Sources & evidence

ORD record
ord-c7e8452651f447d68fc659f4ce599340
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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