Methanol → HCID 57742537, compound

HRID 2266484Notes

Reaction equation

HRID 2266484 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][C:5]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]2[C:6]=1[C:7]([CH3:28])=[C:8]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=1)[C:9]([CH3:16])=[N:10]2.CO.[OH-].[Na+]>C(O)=O>[Cl:15][C:12]1[CH:13]=[CH:14][C:5]([CH2:4][C:3]([OH:29])=[O:2])=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:16])[C:8]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([CH3:27])(=[O:25])=[O:26])=[CH:22][CH:23]=1)=[C:7]2[CH3:28]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68782569HCID 68782569, compound

Product 1

HCID 57742537HCID 57742537, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of [8-chloro-3-(4-methanesulfonylbenzyl)-2,4-dimethylquinolin-5-yl]acetic acid methyl ester (0.050 g), methanol (3.0 mL) and 1.0 M aqueous sodium hydroxide solution (0.63 mL) was stirred at room temperature for 18 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 70% of organic modifier) gave title compound as a white solid, 0.0060 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-501e6065d40d43f7bcc64d95fafc1b08
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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