Hydrochloric Acid → HCID 23114614, compound

HRID 2080436Notes

Reaction equation

HRID 2080436 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])[C:12]2[N:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]([O:22]C)=[O:21])=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])[C:12]2[N:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21])=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23114645HCID 23114645, compound

Product 1

HCID 23114614HCID 23114614, compoundYield 6.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A tetrahydrofuran solution (5 ml) of the methyl(E)-3-[6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]acrylate (460 mg, 0.991 mmol) obtained in Example 44 was added a 1N sodium hydroxide solution (3.0 ml). The resulting mixture was stirred at room temperature for 4 hours. The reaction mixture was acidified with 1N hydrochloric acid, followed by extraction with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate and concentrated. The crude title compound was obtained at a stoichiometric ratio. A portion of the resulting solid was recrystallized from ethyl acetate-hexane to give the title compound (29.4 mg, 0.0653 mmol) as a colorless solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude title compound was obtained at a stoichiometric ratio
  6. customA portion of the resulting solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-e0f77690405a45aa8f27269e1c4bc5ff
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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