Hydrochloric Acid → [3-(4-chlorobenzyl)-4-difluoromethoxy-8-fluoro-2-methylquinolin-5-yloxy]acetic Acid
Reaction equation
C[O:2][C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:26][CH:27]([F:29])[F:28])=[C:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[C:10]([CH3:17])=[N:11]2.CO.[OH-].[Li+].Cl>O1CCCC1.O>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][C:9]2[C:10]([CH3:17])=[N:11][C:12]3[C:7]([C:8]=2[O:26][CH:27]([F:29])[F:28])=[C:6]([O:5][CH2:4][C:3]([OH:30])=[O:2])[CH:15]=[CH:14][C:13]=3[F:16])=[CH:24][CH:23]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of [3-(4-chlorobenzyl)-4-difluoromethoxy-8-fluoro-2-methylquinolin-5-yloxy]acetic acid methyl ester (0.18 g), methanol (3.5 mL), water (2.0 mL), tetrahydrofuran (3.5 mL) and lithium hydroxide solution (0.036 g) was stirred at room temperature for 30 minutes. The solution was acidified by the addition of 1.0 M aqueous hydrochloric acid, extracted with ethyl acetate and the combined extracts dried over sodium sulfate. The solvent was removed under reduced pressure and purification of the residue by preparative reverse-phase HPLC, using a gradient over 30 minutes of acetonitrile in water, gave title compound as a yellow solid, 0.088 g.
Workup
- extractionextracted with ethyl acetate
- dry with materialthe combined extracts dried over sodium sulfate
- customThe solvent was removed under reduced pressure and purification of the residue by preparative reverse-phase HPLC
- customover 30 minutes
Sources & evidence
- ORD record
- ord-37a9fdbb13174da7aabe1c075977c239
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07858640B2
Reaction notes
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