Lithium Hydroxide → HCID 58277328, compound

HRID 1949239Notes

Reaction equation

HRID 1949239 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)[N:11]=[C:10]([C:23]([O:25]CC)=[O:24])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Li+]>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)[N:11]=[C:10]([C:23]([OH:25])=[O:24])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58277287HCID 58277287, compound

Product 1

HCID 58277328HCID 58277328, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

2.00 g (5.07 mmol) of the compound of Example 32A are provided in 37 ml of 1,4-dioxane, a solution of 1.07 g (20.0 mmol) of lithium hydroxide in 37 ml of water is added, and the mixture is stirred at room temperature overnight. The mixture is concentrated, a 1N aqueous hydrogen chloride solution is subsequently added to the residue until the pH is acidic, the mixture is extracted with ethyl acetate, and the combined organic phases are dried over sodium sulfate, filtered and concentrated. 0.74 g (40% of theory) of the title compound are obtained.

Workup

  1. concentrationThe mixture is concentrated
  2. additiona 1N aqueous hydrogen chloride solution is subsequently added to the residue until the pH
  3. extractionthe mixture is extracted with ethyl acetate
  4. dry with materialthe combined organic phases are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7aa63326cfaa4eefa03ff8625cff9779
Source dataset
uspto-grants-2013_03
Patent number
US08399682B2

Reaction notes

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