Water → (4RS,5SR)-5-(2-fluoropyridin-4-yl)-4-((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)-1,3-oxazolidin-2-one

HRID 1610499노트

반응식

HRID 1610499 반응식
[F:1][C:2]1[CH:7]=[C:6]([CH:8](O)[CH:9]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:26])([F:25])[CH:22]([F:24])[F:23])[CH:15]=2)C(O)=O)[CH:5]=[CH:4][N:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:35])C=CC=CC=1.C([N:47]([CH2:50]C)CC)C.[OH2:52]>O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[O:52][C:50](=[O:35])[NH:47][CH:9]2[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:25])([F:26])[CH:22]([F:23])[F:24])[CH:15]=2)[CH:5]=[CH:4][N:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 17862120(2RS,3RS)-3-(2-fluoropyridin-4-yl)-3-hydroxy-2-((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)propionic acid

생성물 1

HCID 22261723(4RS,5SR)-5-(2-fluoropyridin-4-yl)-4-((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)-1,3-oxazolidin-2-one수율 69%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (2RS,3RS)-3-(2-fluoropyridin-4-yl)-3-hydroxy-2-((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)propionic acid (2.0 g, 5.11 mmol) in tetrahydrofuran (50 ml) were added diphenylphosphoryl azide (1.21 ml, 5.62 mmol) and triethylamine (1.07 ml, 7.67 mmol), and the mixture was heated under reflux for 2 hrs. The reaction solution was allowed to cool and water (200 ml) was added. The mixture was extracted with ethyl acetate (100 ml×2). The extract was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1). Recrystallization from ethyl acetate-hexane gave (4RS,5SR)-5-(2-fluoropyridin-4-yl)-4-((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)-1,3-oxazolidin-2-one (1.36 g, 69%).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hrs
  3. temperatureto cool
  4. extractionThe mixture was extracted with ethyl acetate (100 ml×2)
  5. washThe extract was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)
  9. customRecrystallization from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-a46b6e7c6d0146f0bfad06e2f84034a6
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982348B2

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