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

HRID 1610371노트

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HRID 1610371 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:8](O)[CH:9]([CH2:13][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:5]=[CH:6][CH:7]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.C([N:44]([CH2:47]C)CC)C.[OH2:49]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:49][C:47](=[O:32])[NH:44][CH:9]2[CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:18][CH:19]=2)[CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22261877(2RS,3RS)-3-(3-fluorophenyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid

생성물 1

HCID 22262213(4RS,5SR)-5-(3-fluorophenyl)-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (2RS,3RS)-3-(3-fluorophenyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid (10.0 g, 29.2 mmol) in tetrahydrofuran (250 ml) were added diphenylphosphoryl azide (6.9 ml, 32.1 mmol) and triethylamine (6.1 ml, 43.8 mmol) and the mixture was heated under reflux for 4 hrs. The reaction solution was allowed to stand at room temperature, water (200 ml) was added, and the mixture was extracted with ethyl acetate (200 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 recrystallized from ethyl acetate-hexane to give (4RS,5SR)-5-(3-fluorophenyl)-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one (8.88 g, 90%).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hrs
  3. customto stand at room temperature
  4. extractionthe mixture was extracted with ethyl acetate (200 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 recrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-5a34a0dc0409411fa5661eabeec7ea0f
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982348B2

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