HCID 59712343, compound → HCID 59712400, compound

HRID 2222443Notes

Reaction equation

HRID 2222443 reaction equation
C(O[CH:5]([C:15]1[CH:20]=[CH:19][NH:18][C:17](=[O:21])[CH:16]=1)[C:6]1([C:11]([O:13][CH3:14])=[O:12])[CH2:10][CH2:9][CH2:8][O:7]1)(=O)C>C(O)(=O)C.[Zn]>[O:21]=[C:17]1[CH:16]=[C:15]([CH2:5][C:6]2([C:11]([O:13][CH3:14])=[O:12])[CH2:10][CH2:9][CH2:8][O:7]2)[CH:20]=[CH:19][NH:18]1

Participants

4

Reactant 1

HCID 59712343HCID 59712343, compound

Product 1

HCID 59712400HCID 59712400, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 3.69 g of methyl 2-[(acetyloxy)(2-oxo-1,2-dihydro-4-pyridinyl)methyl]tetrahydro-2-furancarboxylate in 30 ml of acetic acid was added 8.17 g of zinc, and the mixture was heated under reflux for 24 hours. This procedure was repeated twice. The reaction mixture was cooled, filtered through Celite, and the Celite and the filtrate were washed with ethanol. The combined organic layers were evaporated, and the residue was purified by silica gel column chromatography, to give 1.31 g of the title compound as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered through Celite
  5. washthe Celite and the filtrate were washed with ethanol
  6. customThe combined organic layers were evaporated
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-39369cc94fe14d8b803ab7cc73c6c365
Source dataset
uspto-grants-2008_05
Patent number
US07371777B2

Reaction notes

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