Ethyl Acetate → HCID 19973089, compound

HRID 2380310Notes

Reaction equation

HRID 2380310 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([O:18][CH2:17]1)[CH:10]([F:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12].[NH:19]1[CH:23]=[N:22][CH:21]=[N:20]1.C(OCC)(=O)C>O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:18])([CH2:17][N:19]1[CH:23]=[N:22][CH:21]=[N:20]1)[CH:10]([F:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 92571H-1,2,4-TriazoleHCID 19973074HCID 19973074, compound

Product 1

HCID 19973089HCID 19973089, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.4 g of ethyl 3-(2,4-difluorophenyl)-3,4-epoxy-2-fluorobutyrate (a mixture of diastereomers) and 6.4 g of 1,2,4-triazole was subjected to reaction at 90°-100° C. for 8 hours. To the reaction mixture were then added 10 ml of ethyl acetate and 5 ml of water. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue obtained was purified by a column chromatography (eluant: chloroform/methanol=20/1) to obtain 650 mg of ethyl 3-(2,4-difluorophenyl)-2-fluoro-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butyrate (one of the diastereomers).

Workup

  1. customwas subjected to reaction at 90°-100° C. for 8 hours
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customThe residue obtained
  7. customwas purified by a column chromatography (eluant: chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-657c136d6b2a4835a4ff09892d90a902
Source dataset
uspto-grants-1994_11
Patent number
US05366989

Reaction notes

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