Lithium Hydroxide → [3-(4-Acetylbenzyl)-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy]acetic acid

HRID 1922081Notes

Reaction equation

HRID 1922081 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:29][CH:30]([F:32])[F:31])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26](=[O:28])[CH3:27])=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.[OH-].[Li+]>CO>[C: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:29][CH:30]([F:32])[F:31])=[C:6]([O:5][CH2:4][C:3]([OH:33])=[O:2])[CH:15]=[CH:14][C:13]=3[F:16])=[CH:21][CH:22]=1)(=[O:28])[CH3:27]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66717804[3-(4-Acetylbenzyl)-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy]acetic acid methyl ester

Product 1

HCID 25095815[3-(4-Acetylbenzyl)-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy]acetic acidYield 158.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [3-(4-acetylbenzyl)-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy]acetic acid methyl ester (0.13 g) in methanol (5.0 mL) was treated with 1.0 M aqueous lithium hydroxide solution (0.54 mL), and the resulting mixture was stirred at room temperature for 30 minutes. The mixture was concentrated under reduced pressure, diluted with water and acidified by the addition of 0.1 M aqueous hydrochloric acid. The mixture was extracted with ethyl acetate, and the combined extracts were washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on C-18 column to afford title compound (0.20 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with water
  3. additionacidified by the addition of 0.1 M aqueous hydrochloric acid
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe combined extracts were washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue purified by column chromatography on C-18 column

Sources & evidence

ORD record
ord-c8085adc492247e69c69d4f0a8506470
Source dataset
uspto-grants-2012_05
Patent number
US08173812B2

Reaction notes

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