Hydrochloric Acid → 5-(2,2-Difluoroethoxy)pyrazine-2-carboxylic acid

HRID 1842124Notes

Reaction equation

HRID 1842124 reaction equation
[OH-].[Na+].[F:3][CH:4]([F:17])[CH2:5][O:6][C:7]1[N:8]=[CH:9][C:10]([C:13]([O:15]C)=[O:14])=[N:11][CH:12]=1.Cl.C(OCC)(=O)C>C(O)C.[Cl-].[Na+].O>[F:17][CH:4]([F:3])[CH2:5][O:6][C:7]1[N:8]=[CH:9][C:10]([C:13]([OH:15])=[O:14])=[N:11][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 57827325Methyl 5-(2,2-difluoroethoxy)pyrazine-2-carboxylate

Product 1

HCID 578274665-(2,2-Difluoroethoxy)pyrazine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A 5 N sodium hydroxide solution (266 μL) was added to a solution of methyl 5-(2,2-difluoroethoxy)pyrazine-2-carboxylate obtained in Preparation Example 51-(1) (145 mg) in ethanol (4 mL), and the mixture was stirred at room temperature for one hour. 5 N hydrochloric acid was added to the reaction solution to prepare an acidic solution. Ethyl acetate and brine were added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure to obtain the title compound (92 mg).

Workup

  1. customto prepare an acidic solution
  2. customthe organic layer was separated
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-46c2574d75cd4c1b8ac8139be5e0452b
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

Loading…