Tributylvinyltin → (S)-N-((3-(3-fluoro-4-vinylphenyl)-2-oxooxazolidin-5-yl)methyl)acetamide

HRID 1637842ノート

反応式

HRID 1637842 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][C@H:11]([CH2:13][NH:14][C:15](=[O:17])[CH3:16])[O:10][C:9]2=[O:18])=[CH:4][C:3]=1[F:19].[CH:20]([Sn](CCCC)(CCCC)CCCC)=[CH2:21]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:20]([C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][C@H:11]([CH2:13][NH:14][C:15](=[O:17])[CH3:16])[O:10][C:9]2=[O:18])=[CH:4][C:3]=1[F:19])=[CH2:21]

参加物

5

反応物 2

HCID 81998TributylvinyltinHCID 11222662(S)-N-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide

生成物 1

HCID 53894753(S)-N-((3-(3-fluoro-4-vinylphenyl)-2-oxooxazolidin-5-yl)methyl)acetamide

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of (S)-(-)-N-[[3-[4-iodo-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (5.45 g), vinyltributyltin (5.48 g) and bis(triphenylphosphine)palladium(II) chloride (303 mg) in 1,4-dioxane (72 mL) under N2 is degassed, heated up to reflux, refluxed for seven hours, cooled to ambient temperature and stirred for 12 hours. The mixture is then diluted with ethyl acetate (40 mL) and water (50 mL) and the layers are separated. The aqueous phase is extracted with ethyl acetate (2×30 mL), and the combined organic phase is washed with saline (40 mL), dried over anhydrous magnesium sulfate, concentrated under reduced pressure and triturated with diethyl ether. The resultant precipitate is filtered to give the title compound, mp 165-166° C.

後処理

  1. customis degassed
  2. temperatureheated up
  3. temperatureto reflux
  4. temperaturerefluxed for seven hours
  5. additionThe mixture is then diluted with ethyl acetate (40 mL) and water (50 mL)
  6. customthe layers are separated
  7. extractionThe aqueous phase is extracted with ethyl acetate (2×30 mL)
  8. washthe combined organic phase is washed with saline (40 mL)
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customtriturated with diethyl ether
  12. filtrationThe resultant precipitate is filtered

出典と根拠

ORDレコード
ord-3eb54b74b0c7436eb0e744c4bbdd0c41
出典データセット
uspto-grants-2000_03
特許番号
US06043266

反応ノート

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