Hydrochloric Acid → [2-difluoromethoxy-3-(4-ethanesulfonylbenzyl)-8-fluoro-4-methylquinolin-5-yloxy]acetic Acid

HRID 2266590Notes

Reaction equation

HRID 2266590 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([CH3:33])=[C:9]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([CH2:31][CH3:32])(=[O:30])=[O:29])=[CH:24][CH:23]=1)[C:10]([O:17][CH:18]([F:20])[F:19])=[N:11]2.CO.[OH-].[Li+].Cl>O.O1CCCC1>[F:20][CH:18]([F:19])[O:17][C:10]1[C:9]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([S:28]([CH2:31][CH3:32])(=[O:29])=[O:30])=[CH:26][CH:27]=2)=[C:8]([CH3:33])[C:7]2[C:12](=[C:13]([F:16])[CH:14]=[CH:15][C:6]=2[O:5][CH2:4][C:3]([OH:34])=[O:2])[N:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 68781836[2-difluoromethoxy-3-(4-ethanesulfonylbenzyl)-8-fluoro-4-methylquinolin-5-yloxy]acetic Acid Methyl Ester

Product 1

HCID 57742496[2-difluoromethoxy-3-(4-ethanesulfonylbenzyl)-8-fluoro-4-methylquinolin-5-yloxy]acetic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [2-difluoromethoxy-3-(4-ethanesulfonylbenzyl)-8-fluoro-4-methylquinolin-5-yloxy]acetic acid methyl ester (0.10 g), methanol (2.0 mL), tetrahydrofuran (2.0 mL), water (2.5 mL) and lithium hydroxide (0.017 mg) was stirred at room temperature for 1 hour. The mixture was acidified by the addition of 1.0 M aqueous hydrochloric acid and purified by preparative reverse-phase HPLC, using a gradient over 30 minutes of acetonitrile in water to afford title compound as a white solid, 0.070 g.

Workup

  1. custompurified by preparative reverse-phase HPLC
  2. customover 30 minutes

Sources & evidence

ORD record
ord-67350f7d7ed74889afc29fbdf573d8c3
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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