Lithium hydroxide, monohydrate → 5-(3,3-Difluoro-azetidin-1-yl)-6-(2-methoxy-ethoxy)-pyridine-2-carboxylic acid

HRID 927599Notes

Reaction equation

HRID 927599 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:14][C:13]([F:16])([F:15])[CH2:12]2)=[C:7]([O:17][CH2:18][CH2:19][O:20][CH3:21])[N:6]=1)=[O:4].O.[OH-].[Li+]>C1COCC1.O>[F:16][C:13]1([F:15])[CH2:14][N:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]=2[O:17][CH2:18][CH2:19][O:20][CH3:21])[CH2:12]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 710874515-(3,3-Difluoroazetidin-1-yl)-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 710873745-(3,3-Difluoro-azetidin-1-yl)-6-(2-methoxy-ethoxy)-pyridine-2-carboxylic acidYield 84%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 5-(3,3-difluoroazetidin-1-yl)-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid methyl ester (0.3 g, 1 mmol) and lithium hydroxide monohydrate (0.25 g, 6 mmol) in THF/H2O (30 mL) was stirred at room temperature for 3 h. After removal of the organic solvent, the aqueous phase was extracted with ethyl acetate (20 mL) and then acidified with 6 N hydrochloric acid to pH 2 to form a precipitate which was collected by filtration and dried under reduced pressure to give the target compound (0.24 g, 84%) as off-white solid which was used directly in the next step without further purification; MS (EI): m/e=289.1 [M+H]+.

Workup

  1. customAfter removal of the organic solvent
  2. extractionthe aqueous phase was extracted with ethyl acetate (20 mL)
  3. customto form a precipitate which
  4. filtrationwas collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-5fb3e671370a4c2a9dce6c20321b9662
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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