Hydrochloric Acid → HCID 23114555, compound

HRID 2080516Notes

Reaction equation

HRID 2080516 reaction equation
O1CCCC1.[Cl:6][C:7]1[C:8]([CH:19]([C:33]2[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=2[F:40])[S:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[CH:9][C:10]([CH2:13][CH2:14][C:15]([O:17]C)=[O:16])=[N:11][CH:12]=1.[OH-].[Na+].Cl>CO>[Cl:6][C:7]1[C:8]([CH:19]([C:33]2[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=2[F:40])[S:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:31])([F:30])[F:32])=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[CH:9][C:10]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[N:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 23114641HCID 23114641, compound

Product 1

HCID 23114555HCID 23114555, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a tetrahydrofuran (2 ml) solution of methyl 3-[5-chloro-4-[(2,5-difluorophenyl)(4-trifluoromethylphenylsulfonyl)methyl]pyridin-2-yl]propionate (92 mg, 0.17 mmol) were added methanol (2 ml) and a 1N aqueous solution of sodium hydroxide (2 ml) at 0° C. The resulting mixture was stirred at room temperature for 2 hours. To the reaction mixture was added 1N hydrochloric acid and the product thus obtained was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was washed with ethanol and collected by filtration to give the title compound (61 mg, 0.12 mmol, 68%) as a white solid.

Workup

  1. customat 0° C
  2. customthe product thus obtained
  3. extractionwas extracted with dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe residue thus obtained
  8. washwas washed with ethanol
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-c3c411a6361e4ad5bc0d6829ceaf879f
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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