Ethyl Acetate → HCID 58508929, compound

HRID 454535Notes

Reaction equation

HRID 454535 reaction equation
C([O:8][C:9]1[CH:36]=[C:35]([C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=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>CO.O1CCOCC1.[C].[Pd]>[OH:8][C:9]1[CH:36]=[C:35]([C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=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

6

Reactant 2

HCID 8857Ethyl AcetateHCID 66990994HCID 66990994, compound

Product 1

HCID 58508929HCID 58508929, compoundYield 70.7%

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-3-yl)benzamido)-4-phenylbenzoate (0.13 g) in methanol (2 mL), dioxane (4 mL), and ethyl acetate (4 mL), 10% palladium-carbon (63 mg) was added, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours. 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: 90-40% hexane/ethyl acetate] to obtain 0.077 g of tert-butyl 2-(2-hydroxy-4-(pyridin-3-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: 90-40% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-34754b652947407f8f0954efb1aba3eb
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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