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1,4-Dioxane → Methyl 2-(5-(2-(azetidin-1-yl)ethoxy)-2-hydroxybenzamido)-4-phenylbenzoate

HRID 454696
Notes
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Reaction equation

HRID 454696 reaction equation
[N:1]1([CH2:5][CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]([O:33]CC3C=CC=CC=3)=[C:12]([CH:32]=2)[C:13]([NH:15][C:16]2[CH:25]=[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:23]=[CH:22][C:17]=2[C:18]([O:20][CH3:21])=[O:19])=[O:14])[CH2:4][CH2:3][CH2:2]1.O1CCOCC1>C(OCC)(=O)C.CO.[C].[Pd]>[N:1]1([CH2:5][CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]([OH:33])=[C:12]([CH:32]=2)[C:13]([NH:15][C:16]2[CH:25]=[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:23]=[CH:22][C:17]=2[C:18]([O:20][CH3:21])=[O:19])=[O:14])[CH2:4][CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 312751,4-DioxaneHCID 66990372Methyl 2-(5-(2-(azetidin-1-yl)ethoxy)-2-(benzyloxy)benzamido)-4-phenylbenzoate

Product 1

HCID 58508869Methyl 2-(5-(2-(azetidin-1-yl)ethoxy)-2-hydroxybenzamido)-4-phenylbenzoateYield 45.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalyst2×
HCID 887
Methanol
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution mixture of the obtained methyl 2-(5-(2-(azetidin-1-yl)ethoxy)-2-(benzyloxy)benzamido)-4-phenylbenzoate (0.088 g) in ethyl acetate (1.5 mL), methanol (1.5 mL), and dioxane (1.5 mL), 10% palladium-carbon (0.088 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours. To the reaction mixture, 10% palladium-carbon (0.088 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 3 hours. The insoluble substance was removed by filtration, and then the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue, and the solid substance was collected by filtration to obtain 0.033 g of methyl 2-(5-(2-(azetidin-1-yl)ethoxy)-2-hydroxybenzamido)-4-phenylbenzoate as a light yellow solid.

Workup

  1. additionwas added
  2. stirringby stirring under a hydrogen atmosphere at room temperature for 3 hours
  3. customThe insoluble substance was removed by filtration
  4. customthe solvent was evaporated under reduced pressure
  5. additionDiisopropyl ether was added to the obtained residue
  6. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-0347c22d1ea74f12bb0b0974687cf826
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492582B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes