Lithium Hydroxide → {4-difluoromethoxy-2-ethyl-8-fluoro-3-[4-(pyrrolidine-1-carbonyl)benzyl]quinolin-5-yloxy}acetic Acid
Reaction equation
C[O:2][C:3](=[O:37])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:33][CH:34]([F:36])[F:35])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:27])=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.[OH-].[Li+]>O1CCCC1>[F:36][CH:34]([F:35])[O:33][C:8]1[C:7]2[C:12](=[C:13]([F:16])[CH:14]=[CH:15][C:6]=2[O:5][CH2:4][C:3]([OH:37])=[O:2])[N:11]=[C:10]([CH2:17][CH3:18])[C:9]=1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([N:28]2[CH2:29][CH2:30][CH2:31][CH2:32]2)=[O:27])=[CH:22][CH:21]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of {4-difluoromethoxy-2-ethyl-8-fluoro-3-[4-(pyrrolidine-1-carbonyl)benzyl]quinolin-5-yloxy}acetic acid methyl ester (0.14 g), tetrahydrofuran (3.0 mL) and 1.0 M aqueous lithium hydroxide solution (0.55 mL) was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure and the residue was diluted with water. The pH of mixture was adjusted to 4 by the addition of sodium dihydrogenphosphate and the resulting precipitate was collected by filtration, washed with water and dried to afford title compound, 0.11 g.
Workup
- customThe solvent was removed under reduced pressure
- additionthe residue was diluted with water
- additionThe pH of mixture was adjusted to 4 by the addition of sodium dihydrogenphosphate
- filtrationthe resulting precipitate was collected by filtration
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-ecc990e19924444bb269e03d3c5db8c3
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07858640B2
Reaction notes
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