Water → HCID 18461317, compound

HRID 2303839Notes

Reaction equation

HRID 2303839 reaction equation
C([O:4][CH2:5][C:6]1[N:28]([CH3:29])[C:9]2=[N:10][C:11]([O:14][C:15]3[CH:20]=[C:19]([CH3:21])[C:18]([O:22][C:23](=[O:25])[CH3:24])=[C:17]([CH3:26])[C:16]=3[CH3:27])=[CH:12][CH:13]=[C:8]2[N:7]=1)(=O)C.C[O-].[Na+].O>CO>[C:23]([O:22][C:18]1[C:19]([CH3:21])=[CH:20][C:15]([O:14][C:11]2[N:10]=[C:9]3[N:28]([CH3:29])[C:6]([CH2:5][OH:4])=[N:7][C:8]3=[CH:13][CH:12]=2)=[C:16]([CH3:27])[C:17]=1[CH3:26])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 18461408HCID 18461408, compound

Product 1

HCID 18461317HCID 18461317, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 500 ml of a solution of 26.0 g of 2-acetoxymethyl-5-(4-acetoxy-2,3,5-trimethylphenoxy)-3-methyl-3H-imidazo[4,5-b]pyridine in methanol, a 1.2 ml solution (28%) of sodium methoxide in methanol was added dropwise at −18° C., followed by stirring at the same temperature for one hour. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The extract was washed with saturated saline and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was crystallized from ethanol. The crystals were collected by filtration, whereby 20.5 g of the title compound were obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was crystallized from ethanol
  6. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-feca0f859b10464f973da500db66b77e
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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