Hydrochloric Acid → HCID 23114735, compound

HRID 2080514Notes

Reaction equation

HRID 2080514 reaction equation
[Cl:1][C:2]1[C:3]([CH:14]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12]C)=[O:11])=[N:6][CH:7]=1.[OH-].[Na+].Cl.C(OCC)(=O)C>CO.O1CCCC1>[Cl:1][C:2]1[C:3]([CH:14]([S:23]([C:26]2[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=2)(=[O:24])=[O:25])[C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])=[CH:4][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 23114758HCID 23114758, compound

Product 1

HCID 23114735HCID 23114735, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-[5-chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]propionate (200 mg, 0.400 mmol) in a mixture of methanol (2 ml) and tetrahydrofuran (2 ml) was added a 1N aqueous sodium hydroxide solution (2 ml). The resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was made weakly acidic by the addition of 1N hydrochloric acid, followed by extraction with dichloromethane. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was recrystallized from hexane:ethyl acetate to give the title compound (161 mg, 0.331 mmol, 83%) as a white powder.

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue thus obtained
  5. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-3d913e360d5849b4b46bc016de1fcb89
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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