Lithium Hydroxide → HCID 58277393, compound

HRID 1949242Notes

Reaction equation

HRID 1949242 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:11]=[C:10]([C:20]([O:22]CC)=[O:21])[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:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=3)[N:11]=[C:10]([C:20]([OH:22])=[O:21])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58277431HCID 58277431, compound

Product 1

HCID 58277393HCID 58277393, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

23.0 g (66.7 mmol) of the compound of Example 35A are provided in 100 ml of 1,4-dioxane, 100 ml (200 mmol) of a 2N solution of lithium hydroxide in water are added, and the mixture is stirred at 50° C. for 2 h. The mixture is concentrated, a conc. aqueous hydrogen chloride solution is subsequently added until the pH is acidic, the mixture is extracted with dichloromethane, and the organic phase is dried over magnesium sulfate, filtered and concentrated. The residue is stirred in a little diethyl ether, collected by filtration and dried under high vacuum. 17.8 g (84% of theory) of the title compound are obtained.

Workup

  1. concentrationThe mixture is concentrated
  2. additiona conc. aqueous hydrogen chloride solution is subsequently added 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
  7. stirringThe residue is stirred in a little diethyl ether
  8. filtrationcollected by filtration
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-542012424d9047d889ff9b8065a18c7e
Source dataset
uspto-grants-2013_03
Patent number
US08399682B2

Reaction notes

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