HCID 66990365, compound → HCID 58508883, compound

HRID 454591Notes

Reaction equation

HRID 454591 reaction equation
C([O:8][C:9]1[CH:36]=[CH:35][C:34]([N:37]([CH3:39])[CH3:38])=[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]>[CH3:39][N:37]([CH3:38])[C:34]1[CH:35]=[CH:36][C:9]([OH:8])=[C:10]([CH:33]=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 66990365HCID 66990365, compound

Product 1

HCID 58508883HCID 58508883, compoundYield 69%

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-(dimethylamino)benzamido)-4-phenylbenzoate (0.063 g) in methanol (1.5 mL) and ethyl acetate (2.5 mL), 10% palladium-carbon (32 mg) was added, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours. To the reaction mixture, 10% palladium-carbon (13 mg) was added, followed by stirring under a hydrogen atmosphere at room temperature for 1 hour and 30 minutes. Ethyl acetate was added to the reaction mixture. The insoluble substance was removed by filtration, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 95-85% hexane/ethyl acetate] to obtain 0.036 g of tert-butyl 2-(5-(dimethylamino)-2-hydroxybenzamido)-4-phenylbenzoate.

Workup

  1. additionwas added
  2. stirringby stirring under a hydrogen atmosphere at room temperature for 1 hour and 30 minutes
  3. customThe insoluble substance was removed by filtration
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography [eluent: 95-85% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-e8de75e6a9734034bb810e08af5c689a
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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