Hydrochloric Acid → 5-(((1R)-2,2-difluorocyclopropyl)methoxy)-3-fluoropyridine-2-carboxylic Acid
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]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
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
- extractionthe mixture was extracted with ethyl acetate
- washThe combined organic layer were washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-497ad9b8b8714cd3a7cad1e2139bd6df
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133129B2
Reaction notes
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