Chloroform → HCID 58508678, compound

HRID 454536Notes

Reaction equation

HRID 454536 reaction equation
C([O:8][C:9]1[CH:36]=[C:35]([C:37]2[CH:42]=[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.C(OCC)(=O)C.C(Cl)(Cl)Cl>CO.O1CCOCC1.[C].[Pd]>[OH:8][C:9]1[CH:36]=[C:35]([C:37]2[CH:42]=[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 8857Ethyl AcetateHCID 66989948HCID 66989948, compound

Product 1

HCID 58508678HCID 58508678, compoundYield 101%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution mixture of the obtained tert-butyl 2-(2-(benzyloxy)-4-(pyridin-2-yl)benzamido)-4-phenylbenzoate (0.13 g) in methanol (2 mL), dioxane (2 mL), and ethyl acetate (4 mL), 10% palladium-carbon (67 mg) was added, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours and 30 minutes. Chloroform 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 [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: chloroform] to obtain 0.11 g of tert-butyl 2-(2-hydroxy-4-(pyridin-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
  4. customThe obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: chloroform]

Sources & evidence

ORD record
ord-bb20aa5f91b74ddd8a883778b6ecead0
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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