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

HRID 2266586Notes

Reaction equation

HRID 2266586 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:31][CH:32]([F:34])[F:33])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH2:29][CH3:30])(=[O:28])=[O:27])=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.CO.[OH-].[Li+].Cl>O.O1CCCC1>[F:34][CH:32]([F:33])[O:31][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:35])=[O:2])[N:11]=[C:10]([CH2:17][CH3:18])[C:9]=1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH2:29][CH3:30])(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 68782516[4-difluoromethoxy-3-(4-ethanesulfonylbenzyl)-2-ethyl-8-fluoroquinolin-5-yloxy]acetic Acid Methyl Ester

Product 1

HCID 57742494[4-difluoromethoxy-3-(4-ethanesulfonylbenzyl)-2-ethyl-8-fluoroquinolin-5-yloxy]acetic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [4-difluoromethoxy-3-(4-ethanesulfonylbenzyl)-2-ethyl-8-fluoroquinolin-5-yloxy]acetic acid methyl ester (0.080 g), methanol (2.0 mL), tetrahydrofuran (2.0 mL), water (2.0 mL) and lithium hydroxide (0.006 mg) was stirred at room temperature for 45 minutes. 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 an off-white solid, 0.025 g.

Workup

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

Sources & evidence

ORD record
ord-459a65d39d974b1cbf53644d1d787a49
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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