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

HRID 428756ノート

反応式

HRID 428756 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 five 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 to five the title compound, mp 165-166° C.

出典と根拠

ORDレコード
ord-2ee441844dbd4189ba92cbf3e6da66a3
出典データセット
uspto-grants-2001_11
特許番号
US06313307B1

反応ノート

読み込み中…