Lithium Hydroxide → HCID 16660244, compound

HRID 2266614Notes

Reaction equation

HRID 2266614 reaction equation
C[O:2][C:3](=[O:31])[CH:4]([O:6][C:7]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]2[C:8]=1[C:9]([CH3:30])=[C:10]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[C:11]([O:18][CH:19]([F:21])[F:20])=[N:12]2)[CH3:5].[OH-].[Li+].P([O-])(O)(O)=O.[Na+]>O1CCCC1>[Cl:17][C:14]1[CH:15]=[CH:16][C:7]([O:6][CH:4]([CH3:5])[C:3]([OH:31])=[O:2])=[C:8]2[C:13]=1[N:12]=[C:11]([O:18][CH:19]([F:20])[F:21])[C:10]([CH2:22][C:23]1[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=1)=[C:9]2[CH3:30]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 23672064Monosodium phosphateHCID 68780022HCID 68780022, compound

Product 1

HCID 16660244HCID 16660244, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-[8-chloro-3-(4-chlorobenzyl)-2-difluoromethoxy-4-methylquinolin-5-yloxy]propionic acid methyl ester (0.22 g), tetrahydrofuran (3.0 mL) and 1.0 M aqueous lithium hydroxide solution (1.0 mL) was stirred at room temperature for 3 hours. The mixture was acidified by the addition of sodium dihydrogenphosphate, concentrated under reduced pressure and the residue extracted with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and the solvent removed under reduced pressure to afford title compound, 0.20 g.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionthe residue extracted with ethyl acetate
  3. washThe combined extracts were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-e3917fa1ab0947a39bcbd8e083cf2fc9
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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