Tetrahydrofuran → HCID 58508487, compound

HRID 454558Notes

Reaction equation

HRID 454558 reaction equation
C([O:8][C:9]1[CH:38]=[CH:37][C:36]([C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)=[CH:35][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][C:28]=2[O:33][CH3:34])[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.O1CCCC1>C(OCC)(=O)C.CO.[C].[Pd]>[OH:8][C:9]1[CH:38]=[CH:37][C:36]([C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)=[CH:35][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][C:28]=2[O:33][CH3:34])[CH:24]=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])=[O:12]

Participants

6

Reactant 2

HCID 8028TetrahydrofuranHCID 66991070HCID 66991070, compound

Product 1

HCID 58508487HCID 58508487, compound

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)-5-(pyridin-3-yl)benzamido)-4-(2-methoxyphenyl)benzoate (0.19 g) in ethyl acetate (5.0 mL) and methanol (5.0 mL), 10% palladium-carbon (39 mg) was added, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours. To the reaction mixture, 10% palladium-carbon (39 mg) was added, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours and 30 minutes. Tetrahydrofuran 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 [Kanto Chemical Co., Inc., silica gel 60 (spherical), PSQ100B (spherical), eluent: 100-91% chloroform/methanol] to obtain tert-butyl 2-(2-hydroxy-5-(pyridin-3-yl)benzamido)-4-(2-methoxyphenyl)benzoate as a white solid.

Workup

  1. additionwas added
  2. stirringby stirring under a hydrogen atmosphere at room temperature for 2 hours 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 [Kanto Chemical Co., Inc., silica gel 60 (spherical), PSQ100B (spherical), eluent: 100-91% chloroform/methanol]

Sources & evidence

ORD record
ord-6b403b1573274270871242bb3b2d6407
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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