Hydrochloric Acid → HCID 19973070, compound

HRID 1451942Notes

Reaction equation

HRID 1451942 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:24])([CH2:18][N:19]1[CH:23]=[N:22][CH:21]=[N:20]1)[C:10]([F:17])([F:16])[C:11]([O:13]CC)=[O:12].[OH-].[Na+].C(OCC)(=O)C.Cl>C(O)C.O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:24])([CH2:18][N:19]1[CH:23]=[N:22][CH:21]=[N:20]1)[C:10]([F:16])([F:17])[C:11]([OH:13])=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 19973081HCID 19973081, compound

Product 1

HCID 19973070HCID 19973070, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In 2 ml of ethanol was dissolved 160 mg of ethyl 3-(2,4-difluorophenyl)-2,2-difluoro-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butyrate. To the resulting solution was added 2 ml of a 1N aqueous sodium hydroxide solution at 0°-5° C. The mixture was subjected to reaction at the same temperature for 10 minutes. The reaction mixture was introduced into a mixed solvent consisting of 10 ml of ethyl acetate and 5 ml of water. The resulting solution was adjusted to pH 2.0 with 6N hydrochloric acid. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. Thereafter, the solvent was removed by distillation under reduced pressure. Diethyl ether was added to the residue obtained, and the resulting crystals were collected by filtration to obtain 100 mg of 3-(2,4-difluorophenyl)-2,2-difluoro-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butyric acid.

Workup

  1. customThe mixture was subjected to reaction at the same temperature for 10 minutes
  2. additionThe reaction mixture was introduced into a mixed solvent
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThereafter, the solvent was removed by distillation under reduced pressure
  7. additionDiethyl ether was added to the residue
  8. customobtained
  9. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-d4d49d3de0b44773bd2dcfeb84c34007
Source dataset
uspto-grants-1997_02
Patent number
US05605921

Reaction notes

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