Lithium Hydroxide → HCID 58277279, compound

HRID 1949244Notes

Reaction equation

HRID 1949244 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)=[CH:11][C:10]([C:23]([O:25]CC)=[O:24])=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Li+]>O1CCOCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:20])[F:21])[CH:14]=3)=[CH:11][C:10]([C:23]([OH:25])=[O:24])=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58277375HCID 58277375, compound

Product 1

HCID 58277279HCID 58277279, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

4.50 g (11.9 mmol) of the compound of Example 37A are provided in 107 ml of 1,4-dioxane, 107 ml (214 mmol) of a 2N solution of lithium hydroxide in water are added, and the mixture is stirred at 70° C. for 2 h. The mixture is concentrated, a 2N aqueous hydrogen chloride solution is subsequently added to the residue until the pH is acidic, the mixture is extracted with dichloromethane, and the organic phase is dried over magnesium sulfate, filtered and concentrated. 4.11 g (99% of theory) of the title compound are obtained.

Workup

  1. concentrationThe mixture is concentrated
  2. additiona 2N aqueous hydrogen chloride solution is subsequently added to the residue until the pH
  3. extractionthe mixture is extracted with dichloromethane
  4. dry with materialthe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ce628980024a4b489a656ab00816e81c
Source dataset
uspto-grants-2013_03
Patent number
US08399682B2

Reaction notes

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