Lithium Hydroxide → HCID 58277359, compound

HRID 1949243Notes

Reaction equation

HRID 1949243 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]=[CH:15][C:14]=3[F:19])=[CH:11][C:10]([C:20]([O:22]CC)=[O:21])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.O1CCOCC1.[OH-].[Li+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])=[CH:11][C:10]([C:20]([OH:22])=[O:21])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 58277383HCID 58277383, compound

Product 1

HCID 58277359HCID 58277359, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

2.30 g (6.67 mmol) of the compound of Example 36A are provided in 32 ml of a 2:1 mixture of 1,4-dioxane and water, 17 ml (33.4 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 2N aqueous hydrogen chloride solution is subsequently added to the residue until the pH is acidic, the mixture is extracted with ethyl acetate, and the organic phase is dried over sodium sulfate, filtered and concentrated. The residue is stirred in a little of a mixture of petroleum ether and diethyl ether, collected by filtration and dried under high vacuum. 1.58 g (75% of theory) of the title compound are obtained.

Workup

  1. additionare added
  2. concentrationThe mixture is concentrated
  3. additiona 2N aqueous hydrogen chloride solution is subsequently added to the residue until the pH
  4. extractionthe mixture is extracted with ethyl acetate
  5. dry with materialthe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. stirringThe residue is stirred in a
  9. additionlittle of a mixture of petroleum ether and diethyl ether
  10. filtrationcollected by filtration
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-0abd0e1c8f70485c8216af71f36f9376
Source dataset
uspto-grants-2013_03
Patent number
US08399682B2

Reaction notes

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