Chloroform → HCID 58508750, compound

HRID 454555Notes

Reaction equation

HRID 454555 reaction equation
C([O:8][C:9]1[CH:36]=[C:35]([N:37]2[CH:41]=[CH:40][N:39]=[CH:38]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:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:12])C1C=CC=CC=1.O1CCOCC1.C(Cl)(Cl)Cl>C(OCC)(=O)C.CO.[C].[Pd]>[OH:8][C:9]1[CH:36]=[C:35]([N:37]2[CH:41]=[CH:40][N:39]=[CH:38]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:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:12]

Participants

7

Reactant 3

HCID 6212ChloroformHCID 312751,4-DioxaneHCID 66990077HCID 66990077, compound

Product 1

HCID 58508750HCID 58508750, compoundYield 83.8%

Reagents, catalysts & solvents 3

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

Procedure

To a solution mixture of the obtained tert-butyl 2-(2-(benzyloxy)-4-(1H-imidazol-1-yl)benzamido)-4-phenylbenzoate (0.12 g) in ethyl acetate (3.6 mL), methanol (1.8 mL), and dioxane (1.8 mL), 10% palladium-carbon (61 mg) was added, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours. To the reaction mixture, 10% palladium-carbon (30 mg) was added, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours. Chloroform was added to the reaction mixture, and the insoluble substance was removed by filtration. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: chloroform] to obtain 0.084 g of tert-butyl 2-(2-hydroxy-4-(1H-imidazol-1-yl)benzamido)-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
  5. customthe obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: chloroform]

Sources & evidence

ORD record
ord-0816858066f94b53b945b3ebb027200e
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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