Lithium Hydroxide → HCID 58277425, compound

HRID 1949238Notes

Reaction equation

HRID 1949238 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][CH3:20])[CH:14]=3)=[CH:11][C:10]([C:21]([O:23]CC)=[O:22])=[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][CH3:20])[CH:14]=3)=[CH:11][C:10]([C:21]([OH:23])=[O:22])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58277423HCID 58277423, compound

Product 1

HCID 58277425HCID 58277425, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

1.50 g (4.20 mmol) of the compound of Example 31A are provided in 20 ml of 1,4-dioxane, 20 ml (20 mmol) of a 1N solution of lithium hydroxide in water are added, and the mixture is stirred at 70° C. for 1 h. 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 magnesium sulfate, filtered and concentrated. 1.32 g (92% 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 magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-be192115ba544d7a96935a3a33e1be0f
Source dataset
uspto-grants-2013_03
Patent number
US08399682B2

Reaction notes

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