Chloroform → HCID 58508881, compound

HRID 454538Notes

Reaction equation

HRID 454538 reaction equation
C([O:8][C:9]1[CH:36]=[C:35]([N:37]2[CH:41]=[CH:40][CH:39]=[N: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][CH:39]=[N: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 66990938HCID 66990938, compound

Product 1

HCID 58508881HCID 58508881, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution mixture of the obtained tert-butyl 2-(2-(benzyloxy)-4-(1H-pyrazol-1-yl)benzamido)-4-phenylbenzoate (0.098 g) in ethyl acetate (2 mL), methanol (1 mL), and dioxane (1 mL), 10% palladium-carbon (49 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. The obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: chloroform] to obtain tert-butyl 2-(2-hydroxy-4-(1H-pyrazol-1-yl)benzamido)-4-phenylbenzoate.

Workup

  1. additionwas added
  2. customthe insoluble substance was removed by filtration
  3. customThe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: chloroform]

Sources & evidence

ORD record
ord-37e67506770b44acba75079fb6da5302
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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