HCID 66990969, compound → HCID 136198172, compound

HRID 454553Notes

Reaction equation

HRID 454553 reaction equation
C([O:8][C:9]1[CH:36]=[CH:35][C:34]([C:37]2[O:38][CH:39]=[N:40][N:41]=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>C(OCC)(=O)C.CO.[C].[Pd]>[OH:8][C:9]1[CH:36]=[CH:35][C:34]([C:37]2[O:38][CH:39]=[N:40][N:41]=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 66990969HCID 66990969, compound

Product 1

HCID 136198172HCID 136198172, compoundYield 83.1%

Reagents, catalysts & solvents 3

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

Procedure

To a solution mixture of the obtained tert-butyl 2-(2-(benzyloxy)-5-(1,3,4-oxadiazol-2-yl)benzamido)-4-phenylbenzoate (0.049 g) in ethyl acetate (1 mL) and methanol (1 mL), 10% palladium-carbon (25 mg) 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 diisopropyl ether was added to the obtained residue. The solid substance was collected by filtration to obtain 0.034 g of tert-butyl 2-(2-hydroxy-5-(1,3,4-oxadiazol-2-yl)benzamido)-4-phenylbenzoate as a white solid.

Workup

  1. additionwas added
  2. customthe insoluble substance was removed by filtration
  3. customThe solvent was evaporated under reduced pressure, and diisopropyl ether
  4. additionwas added to the obtained residue
  5. filtrationThe solid substance was collected by filtration

Sources & evidence

ORD record
ord-51ec1e3a22ed4b0caea9dfb3cd939630
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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