3,5-Dinitrobenzoyl chloride → [(1R)-1-[(2R)-2-(2,4-Difluorophenyl)-2-oxiranyl]ethyl]3,5-dinitrobenzoate

HRID 279157

Reaktionsgleichung

Reaktionsgleichung von HRID 279157
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C@H:12]([OH:14])[CH3:13])[CH2:11][O:10]1.[N+:15]([C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([N+:27]([O-:29])=[O:28])[CH:26]=1)[C:21](Cl)=[O:22])([O-:17])=[O:16]>C(Cl)Cl.CN(C)C>[N+:15]([C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([N+:27]([O-:29])=[O:28])[CH:26]=1)[C:21]([O:14][C@@H:12]([C@@:9]1([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[CH2:11][O:10]1)[CH3:13])=[O:22])([O-:17])=[O:16]

Komponenten

5

Edukt 2

HCID 74323,5-Dinitrobenzoyl chlorideHCID 15130436(1R)-1-[2-(2,4-difluorophenyl)-2-oxiranyl]ethanol

Produkt 1

HCID 10691998[(1R)-1-[(2R)-2-(2,4-Difluorophenyl)-2-oxiranyl]ethyl]3,5-dinitrobenzoateAusbeute 46,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1146TrimethylamineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(1R)-1-[2-(2,4-Difluorophenyl)-2-oxiranyl]ethanol (31.5 g) and 3,5-dinitrobenzoyl chloride (40 g) were dissolved in methylene chloride (500 ml), to which trimethylamine (24.1 ml) was added dropwise at ice-bath temperature. After the mixture was stirred at room temperature for 3.5 hours, it was washed with water (150 ml) and 5% sodium bicarbonate aqueous solution successively, dried over magnesium sulfate and concentrated under reduced pressure. The precipitated crystals were filtrated and washed with methylene chloride. The mother liquor and the washings were combined and distilled off under reduced pressure. Ethyl acetate (25 ml) and methanol (300 ml) were added to the residue, and the mixture was cooled in an ice bath. The precipitated crystals were collected by filtration and recrystallized from a mixture of ethyl acetate (25 ml) and methanol (250 ml) to give [(1R)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl] 3,5-dinitrobenzoate (28.7 g) as colorless needles.

Aufarbeitung

  1. additionwas added dropwise at ice-bath temperature
  2. washit was washed with water (150 ml) and 5% sodium bicarbonate aqueous solution successively
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. filtrationThe precipitated crystals were filtrated
  6. washwashed with methylene chloride
  7. distillationdistilled off under reduced pressure
  8. additionEthyl acetate (25 ml) and methanol (300 ml) were added to the residue
  9. temperaturethe mixture was cooled in an ice bath
  10. filtrationThe precipitated crystals were collected by filtration
  11. customrecrystallized from a mixture of ethyl acetate (25 ml) and methanol (250 ml)

Quellen und Nachweise

ORD-Eintrag
ord-80f214634efa4594864ccfbb47b83c3a
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362206B1

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