Lithium Hydroxide → HCID 58277445, compound

HRID 1949233Notes

Reaction equation

HRID 1949233 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]([F:23])([F:22])[F:21])[CH:14]=3)=[CH:11][C:10]([C:24]([O:26]CC)=[O:25])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Li+]>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]([F:23])([F:22])[F:21])[CH:14]=3)=[CH:11][C:10]([C:24]([OH:26])=[O:25])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58277354HCID 58277354, compound

Product 1

HCID 58277445HCID 58277445, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

10.8 g (26.2 mmol) of the compound of Example 26A are provided in 236 ml of 1,4-dioxane, 236 ml (472 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 and 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. 9.90 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-111042a3a74b424baf74afc6488435fc
Source dataset
uspto-grants-2013_03
Patent number
US08399682B2

Reaction notes

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