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

HRID 1610466
ノート
印刷プレビュー

反応式

HRID 1610466 の反応式
[OH:1][CH:2]([C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:20][CH:19]=1)[CH:3]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1)C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C([N:50]([CH2:53]C)CC)C.[OH2:55]>O1CCCC1>[O:24]([C:21]1[CH:20]=[CH:19][C:18]([CH:2]2[O:1][C:53](=[O:55])[NH:50][CH:3]2[CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:15])([F:17])[F:16])=[CH:10][CH:9]=2)=[CH:23][CH:22]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 17862124(2RS,3RS)-3-hydroxy-3-(4-phenoxyphenyl)-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid

生成物 1

HCID 22261393(4RS,5SR)-5-(4-phenoxyphenyl)-4-((4-(trifluoromethyl)phenyl)-methyl)-1,3-oxazolidin-2-one収率 92%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (2RS,3RS)-3-hydroxy-3-(4-phenoxyphenyl)-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid (7.0 g, 16.8 mmol) in tetrahydrofuran (180 ml) were added diphenylphosphoryl azide (4.0 ml,18.5 mmol) and triethylamine (3.5 ml, 25.2 mmol), and the mixture was heated under reflux for 6 hrs. The reaction solution was allowed to cool and water (200 ml) was added. 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 purified by silica gel-column chromatography (ethyl acetate) and recrystallized from ethyl acetate-hexane to give (4RS,5SR)-5-(4-phenoxyphenyl)-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one (6.40 g, 92%).

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hrs
  3. temperatureto cool
  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 purified by silica gel-column chromatography (ethyl acetate)
  9. customrecrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-79c609a31990492da6dd981ba8be02ed
出典データセット
uspto-grants-2006_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06982348B2

反応ノート

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