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Hydrochloric Acid → 5-(((1R)-2,2-difluorocyclopropyl)methoxy)-3-fluoropyridine-2-carboxylic Acid

HRID 2277302
Notes
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Reaction equation

HRID 2277302 reaction equation
[F:1][C:2]1([F:19])[CH2:4][C@@H:3]1[CH2:5][O:6][C:7]1[CH:8]=[C:9]([F:18])[C:10]([C:13]([O:15]CC)=[O:14])=[N:11][CH:12]=1.C1COCC1.[OH-].[Li+].Cl>C(O)C>[F:19][C:2]1([F:1])[CH2:4][C@@H:3]1[CH2:5][O:6][C:7]1[CH:8]=[C:9]([F:18])[C:10]([C:13]([OH:15])=[O:14])=[N:11][CH:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86731383ethyl 5-(((1R)-2,2-difluorocyclopropyl)methoxy)-3-fluoropyridine-2-carboxylate

Product 1

HCID 867313845-(((1R)-2,2-difluorocyclopropyl)methoxy)-3-fluoropyridine-2-carboxylic AcidYield 81.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of ethyl 5-(((1R)-2,2-difluorocyclopropyl)methoxy)-3-fluoropyridine-2-carboxylate (808 mg), THF (10 mL), ethanol (10 mL) and 1M lithium hydroxide (10 mL) was stirred at 0° C. for 2 hr. The reaction mixture was neutralized with 1M hydrochloric acid at 0° C., and the mixture was extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (594 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layer were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-497ad9b8b8714cd3a7cad1e2139bd6df
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09133129B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes