Methanol → HCID 57742523, compound

HRID 2266443Notes

Reaction equation

HRID 2266443 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]([F:29])[F:28])=[C:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[C:10]([CH3:17])=[N:11]2.CO.[OH-].[Li+]>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]([Cl:25])=[CH:23][CH:24]=1)=[C:8]2[O:26][CH:27]([F:29])[F:28]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 68780083HCID 68780083, compound

Product 1

HCID 57742523HCID 57742523, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of [8-chloro-3-(4-chlorobenzyl)-4-difluoromethoxy-2-methylquinolin-5-yloxy]acetic acid methyl ester (0.10 g), methanol (6.0 mL), water (0.6 mL) and saturated aqueous lithium hydroxide solution (0.3 mL) was stirred at room temperature for 17 hours. The methanol was removed under reduced pressure and the pH of the residue adjusted to 4 by the addition of glacial acetic acid. The resulting precipitate was collected by filtration and washed with water. Purification of the solid by preparative reverse-phase HPLC using a gradient over 37 minutes of acetonitrile in water (20% to 95% of organic modifier) gave title compound as a cream solid, 0.020 g.

Workup

  1. customThe methanol was removed under reduced pressure
  2. additionthe pH of the residue adjusted to 4 by the addition of glacial acetic acid
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water
  5. customPurification of the solid by preparative reverse-phase
  6. customover 37 minutes

Sources & evidence

ORD record
ord-7f85c234be7140ad89b12f229eef0173
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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