Methanol → HCID 57742541, compound

HRID 2266496Notes

Reaction equation

HRID 2266496 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([O:26][CH:27]([CH3:29])[CH3:28])=[C:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:10]([CH3:17])=[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:30])=[O:2])=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:17])[C:9]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=1)=[C:8]2[O:26][CH:27]([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68783077HCID 68783077, compound

Product 1

HCID 57742541HCID 57742541, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of [8-chloro-3-(4-fluorobenzyl)-4-isopropoxy-2-methylquinolin-5-yloxy]acetic acid methyl ester (0.020 g), methanol (1.0 mL) and 1.0 M aqueous sodium hydroxide solution (0.25 mL) was stirred at room temperature for 3 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 over 30 minutes of acetonitrile in water (30% to 90% of organic modifier) gave title compound as a pale yellow solid, 0.012 g.

Workup

  1. customthe solvent removed under reduced pressure
  2. customPurification of the residue by preparative reverse-phase
  3. customover 30 minutes

Sources & evidence

ORD record
ord-86032aa0f8d6459ab86ba26b714db922
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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