Lithium Hydroxide → HCID 67332171, compound

HRID 2289099Notes

Reaction equation

HRID 2289099 reaction equation
C[CH:2]([C:6]1[CH:11]=[CH:10][C:9]([S:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]3[CH:21]([C:29]([F:32])([F:31])[F:30])[N:22]([CH2:26][CH2:27][CH3:28])[O:23][C:24]=3[CH:25]=2)=[C:8]([Cl:33])[CH:7]=1)[C:3]([OH:5])=[O:4].[OH-].[Li+]>CO.O>[Cl:33][C:8]1[CH:7]=[C:6]([CH2:2][C:3]([OH:5])=[O:4])[CH:11]=[CH:10][C:9]=1[S:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]2[CH:21]([C:29]([F:31])([F:30])[F:32])[N:22]([CH2:26][CH2:27][CH3:28])[O:23][C:24]=2[CH:25]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69969404HCID 69969404, compound

Product 1

HCID 67332171HCID 67332171, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl 3-chloro-4-(3-(2-propyl-3-trifluoromethyl-6-benz-[4,5]-isoxazoloxy)propylthio)phenylacetic acid (0.113 grams) in methanol (1.5 mL) was treated with a solution of lithium hydroxide in water (1.01 M; 0.362 mL). The reaction was refluxed 1 hour. The reaction mixture was partitioned between isopropyl acetate and 0.1N HCl. The organic was dried over magnesium sulfate, filtered and concentrated to a solid. The solid was suspended in methylene chloride/cyclohexane (1:1; 2 mL). The mixture was refluxed briefly and cooled to 0° C. The title compound was isolated by filtration.

Workup

  1. temperatureThe reaction was refluxed 1 hour
  2. customThe reaction mixture was partitioned between isopropyl acetate and 0.1N HCl
  3. dry with materialThe organic was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a solid
  6. temperatureThe mixture was refluxed briefly

Sources & evidence

ORD record
ord-452944f7f3ac49c09c54c000be7c678b
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

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