Lithium Hydroxide → HCID 25096333, compound

HRID 1922116Notes

Reaction equation

HRID 1922116 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([CH3:34])=[C:9]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:24][CH:23]=1)[C:10]([O:17][CH:18]([F:20])[F:19])=[N:11]2.[OH-].[Li+]>O1CCCC1.O>[Cl:16][C:13]1[CH:14]=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:35])=[O:2])=[C:7]2[C:12]=1[N:11]=[C:10]([O:17][CH:18]([F:19])[F:20])[C:9]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:33])[C:29]([CH3:30])([CH3:31])[CH3:32])=[CH:24][CH:23]=1)=[C:8]2[CH3:34]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67458485HCID 67458485, compound

Product 1

HCID 25096333HCID 25096333, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of {8-chloro-2-difluoromethoxy-3-[4-(2,2-dimethylpropionyl)benzyl]-4-methylquinolin-5-yloxy}acetic acid methyl ester (0.18 g) in tetrahydrofuran (10 mL) and water (1.5 mL) was treated with 1.0 M aqueous lithium hydroxide solution (0.71 mL), and the resulting mixture was stirred at room temperature for 2 hours. The mixture was concentrated under reduced pressure, diluted with water and dichloromethane and then acidified by the addition of 0.1 M aqueous hydrochloric acid solution. The aqueous phase was extracted with dichloromethane and the combined organic phases dried over magnesium sulfate. The solvent was removed under reduced pressure to give title compound as a white solid (0.16 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with water and dichloromethane
  3. additionacidified by the addition of 0.1 M aqueous hydrochloric acid solution
  4. extractionThe aqueous phase was extracted with dichloromethane
  5. dry with materialthe combined organic phases dried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-da08d3a92acd414a8b9f723c009ff89a
Source dataset
uspto-grants-2012_05
Patent number
US08173812B2

Reaction notes

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