Triethylamine → (4RS,5SR)-4-((4-fluorophenyl)methyl)-5-(4-(trifluoromethyl)phenyl)-1,3-oxazolidin-2-one

HRID 1610475노트

반응식

HRID 1610475 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH:13]([OH:24])[C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)C(O)=O)=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.C([N:44]([CH2:47]C)CC)C>O1CCCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]2[CH:13]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:21])([F:23])[F:22])=[CH:16][CH:15]=3)[O:24][C:47](=[O:32])[NH:44]2)=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 17862204(2RS,3RS)-2-((4-fluorophenyl)methyl)-3-hydroxy-3-(4-(trifluoromethyl)phenyl)propionic acid

생성물 1

HCID 22261770(4RS,5SR)-4-((4-fluorophenyl)methyl)-5-(4-(trifluoromethyl)phenyl)-1,3-oxazolidin-2-one수율 92.4%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (2RS,3RS)-2-((4-fluorophenyl)methyl)-3-hydroxy-3-(4-(trifluoromethyl)phenyl)propionic acid (21.0 g, 61.35 mmol) in tetrahydrofuran (500 ml) were added diphenylphosphoryl azide (14.5 ml, 67.5 mmol) and triethylamine (12.9 ml, 92 mmol), and the mixture was heated under reflux for 3 hrs. The reaction solution was diluted with water (500 ml), and the mixture was extracted with ethyl acetate (500 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate). Recrystallization from ethyl acetate-hexane gave (4RS,5SR)-4-((4-fluorophenyl)methyl)-5-(4-(trifluoromethyl)phenyl)-1,3-oxazolidin-2-one (19.24 g, 92%).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hrs
  3. extractionthe mixture was extracted with ethyl acetate (500 ml×2)
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  8. customRecrystallization from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-b9ff729f76d349ce8b92eb413db3da33
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982348B2

반응 노트

불러오는 중…