Methanol → HCID 57742533, compound

HRID 2266478Notes

Reaction equation

HRID 2266478 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([O:29][CH:30]([F:32])[F:31])=[C:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1)[C:10]([CH3:17])=[N:11]2.CO.[OH-].[Li+].O>C(O)(=O)C>[Cl:16][C:13]1[CH:14]=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:33])=[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]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:23][CH:24]=1)=[C:8]2[O:29][CH:30]([F:31])[F:32]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 68783486HCID 68783486, compound

Product 1

HCID 57742533HCID 57742533, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of [8-chloro-4-difluoromethoxy-3-(4-methanesulfonylbenzyl)-2-methylquinolin-5-yloxy]acetic acid methyl ester (0.13 g), methanol (20 mL), saturated, aqueous lithium hydroxide solution (1.0 mL) and water (2.0 mL) was stirred at room temperature for 45 minutes. The pH of the solution was adjusted to 5 by the addition of glacial acetic acid and the methanol removed under reduced pressured. The resulting precipitate was collected by filtration and purified by preparative reverse-phase HPLC using a gradient over 45 minutes of acetonitrile in water (10% to 95% of organic modifier) to afford title compound as a pale yellow solid, 0.014 g.

Workup

  1. customthe methanol removed
  2. filtrationThe resulting precipitate was collected by filtration
  3. custompurified by preparative reverse-phase
  4. customover 45 minutes

Sources & evidence

ORD record
ord-bf3785d31b914e75b020dd370ae742d4
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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