Lithium Hydroxide → [3-(4-chloro-2-fluorobenzyl)-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy]acetic Acid

HRID 2266596Notes

Reaction equation

HRID 2266596 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:28][CH:29]([F:31])[F:30])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[F:27])[C:10]([CH2:17][CH3:18])=[N:11]2.[OH-].[Li+]>O1CCCC1>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][C:9]2[C:10]([CH2:17][CH3:18])=[N:11][C:12]3[C:7]([C:8]=2[O:28][CH:29]([F:30])[F:31])=[C:6]([O:5][CH2:4][C:3]([OH:32])=[O:2])[CH:15]=[CH:14][C:13]=3[F:16])=[C:21]([F:27])[CH:22]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68782553[3-(4-chloro-2-fluorobenzyl)-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy]acetic Acid Methyl Ester

Product 1

HCID 16660088[3-(4-chloro-2-fluorobenzyl)-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy]acetic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [3-(4-chloro-2-fluorobenzyl)-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy]acetic acid methyl ester (0.071 g), tetrahydrofuran (5.0 mL) and 1.0 M aqueous lithium hydroxide solution (0.30 mL) was stirred at room temperature for 2 hour. The solvent was removed under reduced pressure and the residue was diluted with water. The pH of mixture was adjusted to 4 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 to afford title compound, 0.064 g.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with water
  3. additionThe pH of mixture was adjusted to 4 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

Sources & evidence

ORD record
ord-8be6064cba9441e48383b0f72b09fdd1
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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