Lithium Hydroxide → HCID 58277293, compound

HRID 1949260Notes

Reaction equation

HRID 1949260 reaction equation
[Cl: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>[Cl: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 58277319HCID 58277319, compound

Product 1

HCID 58277293HCID 58277293, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

4.75 g (12.0 mmol) of the compound of Example 55A are provided in 108 ml of 1,4-dioxane, 108 ml (216 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 conc. 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. 4.40 g (100% of theory) of the title compound are obtained.

Workup

  1. concentrationThe mixture is concentrated
  2. additiona conc. 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-b63215a9fbb84e6d90d370b4a1a08dca
Source dataset
uspto-grants-2013_03
Patent number
US08399682B2

Reaction notes

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