Hydrochloric Acid → HCID 19973098, compound

HRID 2380313Notes

Reaction equation

HRID 2380313 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](OCC)=[O:12].[CH3:25][CH:26]1[O:31][CH:30]([CH3:32])[CH2:29][NH:28][CH2:27]1.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:17])([F:16])[C:11]([N:28]1[CH2:27][CH:26]([CH3:25])[O:31][CH:30]([CH3:32])[CH2:29]1)=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 1108622,6-DimethylmorpholineHCID 19973081HCID 19973081, compound

Product 1

HCID 19973098HCID 19973098, compoundYield 8.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In 1 ml of ethanol was dissolved 100 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 330 mg of 2,6-dimethylmorpholine. The resulting mixture was subjected to reaction for 2 hours under reflux. Then, the reaction mixture was introduced into a mixed solvent consisting of 20 ml of ethyl acetate and 10 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. The residue obtained was purified by a column chromatography (eluant: chloroform) to obtain 10 mg of 4-[3-(2,4-difluorophenyl)-2,2-difluoro-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butanoyl]-2,6-dimethylmorpholine.

Workup

  1. customThe resulting mixture was subjected to reaction for 2 hours
  2. temperatureunder reflux
  3. additionThen, the reaction mixture was introduced into a mixed solvent
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThereafter, the solvent was removed by distillation under reduced pressure
  8. customThe residue obtained
  9. customwas purified by a column chromatography (eluant: chloroform)

Sources & evidence

ORD record
ord-8d84d7dfc43b4480b36e1cb52b7724e1
Source dataset
uspto-grants-1994_11
Patent number
US05366989

Reaction notes

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