Sodium Hydroxide → [8-chloro-3-(2-chloro-4-methanesulfonylbenzyl)-2,4-dimethylquinolin-5-yloxy]acetic Acid

HRID 2266518Notes

Reaction equation

HRID 2266518 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]([CH3:30])=[C:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][C:20]=1[Cl:29])[C:10]([CH3:17])=[N:11]2.[OH-].[Na+]>CO>[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]([CH3:17])[C:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][C:20]=1[Cl:29])=[C:8]2[CH3:30]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68782003HCID 68782003, compound

Product 1

HCID 57742499[8-chloro-3-(2-chloro-4-methanesulfonylbenzyl)-2,4-dimethylquinolin-5-yloxy]acetic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [8-chloro-3-(2-chloro-4-methanesulfonylbenzyl)-2,4-dimethylquinolin-5-yloxy]acetic acid methyl ester (0.36 g), methanol (10 mL) and 1.0 M aqueous sodium hydroxide solution (4.0 mL) was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure and the pH of the residue adjusted to 5 by the addition of formic acid. Purification by preparative reverse-phase HPLC using a gradient of acetonitrile in water (50% to 65% of organic modifier) gave title compound as a white solid, 0.035 g.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe pH of the residue adjusted to 5 by the addition of formic acid
  3. customPurification by preparative reverse-phase

Sources & evidence

ORD record
ord-985163cd190f41cc894f2b6631079068
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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