Hydrochloric Acid → 2-(4-(5-(3, 5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydroisoxazol-3-yl)-2-methylbenzamido )acetic acid

HRID 910380Notes

Reaction equation

HRID 910380 reaction equation
C[N:2]([C:7](=[O:32])[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH2:18][C:17]([C:23]3[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=3)([C:19]([F:22])([F:21])[F:20])[O:16][N:15]=2)=[CH:10][C:9]=1[CH3:31])[CH2:3][C:4]([OH:6])=[O:5].[OH-].[K+].Cl>CO.O>[Cl:30][C:25]1[CH:24]=[C:23]([C:17]2([C:19]([F:21])([F:20])[F:22])[O:16][N:15]=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([C:7]([NH:2][CH2:3][C:4]([OH:6])=[O:5])=[O:32])=[C:9]([CH3:31])[CH:10]=3)[CH2:18]2)[CH:28]=[C:27]([Cl:29])[CH:26]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 66784990HCID 66784990, compound

Product 1

HCID 231598052-(4-(5-(3, 5-dichlorophenyl)-5-(trifluoromethyl)-4, 5-dihydroisoxazol-3-yl)-2-methylbenzamido )acetic acidYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In a solution of 2.6 g of methyl N-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoyl]glycine (Compound of the present invention No. 5-128) synthesized similarly to Synthetic Example 5 in 10 ml of methanol, a solution of 1.0 g of potassium hydroxide in 10 ml of water was added with stirring at room temperature, and stirred at the same temperature for further 1 hour. After the completion of the reaction, 10 ml of 12N hydrochloric acid was added and extracted with ethyl acetate (50 ml×1), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 2.4 g of the aimed product as pale yellow resinous resinous substance.

Workup

  1. stirringstirred at the same temperature for further 1 hour
  2. additionwas added
  3. extractionextracted with ethyl acetate (50 ml×1)
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-91a3e791c47742dcbed2fefdfa897f69
Source dataset
uspto-grants-2011_09
Patent number
US08022089B2

Reaction notes

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