Lithium Hydroxide → HCID 23436555, compound

HRID 2121232Notes

Reaction equation

HRID 2121232 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:6][C:5]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]([F:27])([F:26])[F:25].[Li+].[OH-]>CO>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:28])=[O:2])=[C:5]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:25])([F:27])[F:26])[CH:6]=2)[CH:13]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10810240HCID 10810240, compound

Product 1

HCID 23436555HCID 23436555, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of Example 304D (241 mg, 0.62 mmol) was dissolved in methanol (5 mL) and saturated aqueous LiOH (1 mL) was added. The reaction was heated at reflux for 1 hour. The reaction mixture was then evaporated and fomlic acid (1 mL) was added to acidify the crude product to pH3. The reaction was evaporated again to remove formic acid and ethyl acetate (5 mL) and H2O (1 mL) were added to completely solubilize the reaction mixture. The aqueous layer was extracted with ethyl acetate (3×) and the ethyl acetate layers were combined and dried over Na2SO4, filtered and evaporated to give the acid (231 mg, 100%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 1 hour
  3. customThe reaction mixture was then evaporated
  4. additionfomlic acid (1 mL) was added
  5. customThe reaction was evaporated again
  6. customto remove formic acid and ethyl acetate (5 mL) and H2O (1 mL)
  7. additionwere added
  8. extractionThe aqueous layer was extracted with ethyl acetate (3×)
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-24a014a4139e4182a169450e4edeafc4
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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