Lithium Hydroxide → Pexopiprant
Reaction equation
C[O:2][C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([O:27][CH:28]([F:30])[F:29])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.[OH-].[Li+]>O1CCCC1>[Cl:16][C:13]1[CH:14]=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:31])=[O:2])=[C:7]2[C:12]=1[N:11]=[C:10]([CH2:17][CH3:18])[C:9]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=1)=[C:8]2[O:27][CH:28]([F:30])[F:29]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of [8-chloro-3-(4-chlorobenzyl)-4-difluoromethoxy-2-ethylquinolin-5-yloxy]acetic acid methyl ester (0.017 g), tetrahydrofuran (3.0 mL) and 1.0 M aqueous lithium hydroxide solution (0.20 mL) was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure and the residue diluted with water. The pH of the resulting mixture was adjusted to 5 by the addition of sodium dihydrogenphosphate and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and the solvent removed under reduced pressure. Purification of the residue by preparative reverse-phase HPLC using a gradient of acetonitrile in water (30% to 95% of organic modifier) gave title compound, 0.010 g.