Acetic Acid → HCID 58508556, compound

HRID 454578Notes

Reaction equation

HRID 454578 reaction equation
O.C([O-])=O.[Na+].C(O)(=O)C.C([O:17][C:18]1[CH:41]=[CH:40][C:39]([N:42]2[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)=[CH:38][C:19]=1[C:20]([NH:22][C:23]1[CH:32]=[C:31]([C:33]2[O:34][CH:35]=[CH:36][CH:37]=2)[CH:30]=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26])=[O:21])C1C=CC=CC=1>[C].[Pd].O1CCOCC1>[O:34]1[CH:35]=[CH:36][CH:37]=[C:33]1[C:31]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([NH:22][C:20](=[O:21])[C:19]2[CH:38]=[C:39]([N:42]3[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]3)[CH:40]=[CH:41][C:18]=2[OH:17])[CH:32]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 2723810Sodium FormateHCID 66990298HCID 66990298, compound

Product 1

HCID 58508556HCID 58508556, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 312751,4-DioxaneSolvent

Procedure

Water (0.20 mL), sodium formate (0.045 g), acetic acid (0.043 mL) and 10% palladium-carbon (8 mg) were added to a dioxane (1 mL) solution of methyl 2-(2-(benzyloxy)-5-(piperidin-1-yl)benzamido)-4-(furan-2-yl)benzoate (0.085 g), followed by stirring at room temperature for 3 hours and 30 minutes and then at 60° C. for 50 minutes. To the reaction mixture, 10% palladium-carbon (8 mg) was added, followed by stirring at 70° C. for 50 minutes. After cooling the reaction mixture to room temperature, the insoluble substance was removed by filtration, and 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 0.048 g of methyl 4-(furan-2-yl)-2-(2-hydroxy-5-(piperidin-1-yl)benzamido)benzoate.

Workup

  1. waitat 60° C. for 50 minutes
  2. stirringby stirring at 70° C. for 50 minutes
  3. temperatureAfter cooling the reaction mixture to room temperature
  4. customthe insoluble substance was removed by filtration
  5. customthe solvent was evaporated under reduced pressure
  6. additionDiisopropyl ether was added to the obtained residue
  7. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-8e5fbb37d83e406fa893e91723cae2d3
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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