HCID 66990683, compound → HCID 58508892, compound

HRID 454541Notes

Reaction equation

HRID 454541 reaction equation
C([O:8][C:9]1[C:10]([C:19]([NH:21][C:22]2[CH:34]=[C:33]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:32]=[CH:31][C:23]=2[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:20])=[CH:11][C:12]2[O:17][CH2:16][CH2:15][O:14][C:13]=2[CH:18]=1)C1C=CC=CC=1>CO.C(OCC)(=O)C.[C].[Pd]>[OH:8][C:9]1[C:10]([C:19]([NH:21][C:22]2[CH:34]=[C:33]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:32]=[CH:31][C:23]=2[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:20])=[CH:11][C:12]2[O:17][CH2:16][CH2:15][O:14][C:13]=2[CH:18]=1

Participants

5

Reactant 1

HCID 66990683HCID 66990683, compound

Product 1

HCID 58508892HCID 58508892, compoundYield 90.7%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution mixture of the obtained tert-butyl 2-(7-(benzyloxy)-2,3-dihydrobenzo[1,4]dioxine-6-carboxamido)-4-phenylbenzoate (0.49 g) in methanol (4 mL) and ethyl acetate (4 mL), 10% palladium-carbon (0.24 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 to obtain 0.37 g of tert-butyl 2-(7-hydroxy-2,3-dihydrobenzo[1,4]dioxine-6-carboxamido)-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
  4. additionDiisopropyl ether was added to the obtained residue
  5. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-016ad473bf9f45f59f8bfc863524d48d
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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