Water → HCID 68535543, compound

HRID 2389364Notes

Reaction equation

HRID 2389364 reaction equation
[C:1]1([CH:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:23])[N:12]([CH2:14][CH2:15][O:16]C3CCCCO3)[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC(N=NC2C=CC(N)=NC=2N)=CC=1.Cl.CC1C=CC(S(O)(=O)=O)=CC=1.O>CO>[C:24]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:23])[N:12]([CH2:14][CH2:15][OH:16])[CH:13]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21909214Pyridium p-toluenesulfonateHCID 68533618HCID 68533618, compound

Product 1

HCID 68535543HCID 68535543, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of 5-(diphenylmethyl)-1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2(1H)-pyridinone (46 mg) in MeOH (1.38 mL) was added pyridium p-toluenesulfonate (9 mg) at ambient temperature. After 48 hours, water was added and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (chloroform:EtOAc=1:2) to give 5-(diphenylmethyl)-1-(2-hydroxyethyl)-2(1H)-pyridinone (20 mg).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by preparative thin-layer chromatography (chloroform:EtOAc=1:2)

Sources & evidence

ORD record
ord-a64a936871004bf48ee2425d88b5df9f
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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