Methanol → HCID 57742527, compound

HRID 2266527Notes

Reaction equation

HRID 2266527 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([CH2:30][CH3:31])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.CO.[OH-].[Na+]>C(O)=O>[Cl:16][C:13]1[CH:14]=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:32])=[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]([S:26]([CH3:29])(=[O:27])=[O:28])=[CH:24][CH:25]=1)=[C:8]2[CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68783790HCID 68783790, compound

Product 1

HCID 57742527HCID 57742527, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of [8-chloro-2,4-diethyl-3-(4-methanesulfonylbenzyl)quinolin-5-yloxy]acetic acid methyl ester (0.20 g), methanol (4.0 mL) and 1.0 M aqueous sodium hydroxide solution (2.0 mL) was stirred at room temperature for 5 hours. The pH of the solution was adjusted to 5 by the addition of formic acid and the solvent removed under reduced pressure. Purification of the residue by preparative reverse-phase HPLC using a gradient of acetonitrile in water (40% to 85% of organic modifier) gave title compound as a pale yellow solid, 0.034 g.

Workup

  1. customthe solvent removed under reduced pressure
  2. customPurification of the residue by preparative reverse-phase

Sources & evidence

ORD record
ord-2b3a3462f4184e44aec4a7e843529008
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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