Acetic Acid → [4-Difluoromethoxy-2-ethyl-8-fluoro-3-(4-methoxybenzyl)quinolin-5-yloxy]acetic acid

HRID 1922074Notes

Reaction equation

HRID 1922074 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:28][CH:29]([F:31])[F:30])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.O.[OH-].[Na+].C(O)(=O)C>CO>[F:31][CH:29]([F:30])[O:28][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:32])=[O:2])[N:11]=[C:10]([CH2:17][CH3:18])[C:9]=1[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 67457390[4-Difluoromethoxy-2-ethyl-8-fluoro-3-(4-methoxybenzyl)quinolin-5-yloxy]acetic acid methyl ester

Product 1

HCID 25095813[4-Difluoromethoxy-2-ethyl-8-fluoro-3-(4-methoxybenzyl)quinolin-5-yloxy]acetic acidYield 29.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [4-difluoromethoxy-2-ethyl-8-fluoro-3-(4-methoxybenzyl)quinolin-5-yloxy]acetic acid methyl ester (0.30 g) in methanol (10 mL), and water (1.0 mL) was treated with 5.0 M aqueous sodium hydroxide solution (0.67 mL) and the resulting mixture was stirred at room temperature for 1 hour. The mixture was acidified by the addition of glacial acetic acid, concentrated under reduced pressure, and the residue purified by preparative reverse-phase HPLC to afford title compound as a pale yellow solid (0.086 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe residue purified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-8251c2179fb048d19bd123079f6f23d0
Source dataset
uspto-grants-2012_05
Patent number
US08173812B2

Reaction notes

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