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

HRID 129113

반응식

HRID 129113 반응식
[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.C(N(CC)CC)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([C@H:12]([O:14][C:21](=[O:22])[C:20]2[CH:19]=[C:18]([N+:15]([O-:17])=[O:16])[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=2)[CH3:13])[CH2:11][O:10]1

참가 물질

5

반응물 2

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

생성물 1

HCID 10691998[(1R)-1-[(2R)-2-(2,4-Difluorophenyl)-2-oxiranyl]ethyl]3,5-dinitrobenzoate수율 46.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

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

후처리

  1. additionwas added dropwise
  2. washwashed with 150 ml of water
  3. dry with materialwith 150 ml of 5% aqueous solution of sodium bicarbonate, dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crystals separated out
  6. filtrationwere collected by filtration
  7. washwashed with methylene chloride
  8. distillationdistilled off under reduced pressure
  9. addition25 ml of ethyl acetate and 300 ml of methanol were added to the residue
  10. temperaturethe mixture was cooled with ice
  11. customThe crystals separated out
  12. filtrationwere collected by filtration
  13. customrecrystallized from a mixture of 25 ml of ethyl acetate and 250 ml of methanol

출처 및 근거

ORD 기록
ord-9f3b944ca2bf4daebaf0cfcbaf2973f1
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05466820

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