Lithium Hydroxide → HCID 25096333, compound

HRID 1944328Notes

Reaction equation

HRID 1944328 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 1.0M 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 0.1M 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 0.1M 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-f1aa71613a2248fabc1931d106bebc16
Source dataset
uspto-grants-2013_03
Patent number
US08394830B2

Reaction notes

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