Hydrochloric Acid → HCID 25096332, compound

HRID 1922111Notes

Reaction equation

HRID 1922111 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:31][CH:32]([F:34])[F:33])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.[OH-].[Li+].Cl>O1CCCC1>[F:34][CH:32]([F:33])[O:31][C:8]1[C:7]2[C:12](=[C:13]([F:16])[CH:14]=[CH:15][C:6]=2[O:5][CH2:4][C:3]([OH:35])=[O:2])[N:11]=[C:10]([CH2:17][CH3:18])[C:9]=1[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86642374HCID 86642374, compound

Product 1

HCID 25096332HCID 25096332, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [4-difluoromethoxy-2-ethyl-8-fluoro-3-(4-trifluoromethoxybenzyl)quinolin-5-yloxy]acetic acid methyl ester (0.054 g) in tetrahydrofuran (4.0 mL) was treated with 1.0 M aqueous lithium hydroxide solution (0.21 mL), and the resulting mixture was stirred at room temperature for 3 hours. The mixture was acidified by the addition of 0.1 M aqueous hydrochloric acid and extracted with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and then concentrated under reduced pressure. Purification of the residue by preparative reverse-phase HPLC gave title compound as a white solid (0.042 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-c1c83c6033624757b8d9d84dded7463d
Source dataset
uspto-grants-2012_05
Patent number
US08173812B2

Reaction notes

Loading…