Lithium Hydroxide → 932708-14-0

HRID 2266521Notes

Reaction equation

HRID 2266521 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([O:27][CH:28]([F:30])[F:29])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.[OH-].[Li+]>O1CCCC1>[Cl:16][C:13]1[CH:14]=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:31])=[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]([Cl:26])=[CH:24][CH:25]=1)=[C:8]2[O:27][CH:28]([F:30])[F:29]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68780330HCID 68780330, compound

Product 1

HCID 16038335932708-14-0

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [8-chloro-3-(4-chlorobenzyl)-4-difluoromethoxy-2-ethylquinolin-5-yloxy]acetic acid methyl ester (0.017 g), tetrahydrofuran (3.0 mL) and 1.0 M aqueous lithium hydroxide solution (0.20 mL) was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure and the residue diluted with water. The pH of the resulting mixture was adjusted to 5 by the addition of sodium dihydrogenphosphate and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and the solvent removed under reduced pressure. Purification of the residue by preparative reverse-phase HPLC using a gradient of acetonitrile in water (30% to 95% of organic modifier) gave title compound, 0.010 g.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue diluted with water
  3. additionThe pH of the resulting mixture was adjusted to 5 by the addition of sodium dihydrogenphosphate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. customthe solvent removed under reduced pressure
  7. customPurification of the residue by preparative reverse-phase

Sources & evidence

ORD record
ord-4cce6ccec8c7432a96a2d3f98d4f8a31
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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