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Tin atom → (S)-N-[[3-[3-fluoro-4-(4-methoxy-5-oxo-1,3,6-cycloheptatrien-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 259817
ノート
印刷プレビュー

反応式

HRID 259817 の反応式
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])[O:11][C:10]2=[O:19])[CH:5]=[CH:6][C:7]=1I.C[Sn](C)(C)[C:22]1[CH:28]=[CH:27][C:26](=[O:29])[C:25]([O:30][CH3:31])=[CH:24][CH:23]=1.[Sn]>O1CCOCC1.[Pd].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>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])[O:11][C:10]2=[O:19])[CH:5]=[CH:6][C:7]=1[C:22]1[CH:28]=[CH:27][C:26](=[O:29])[C:25]([O:30][CH3:31])=[CH:24][CH:23]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 5352426Tin atomHCID 11222662(S)-N-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamideHCID 15312848Trimethyl(4-methoxy-5-oxo-1,3,6-cycloheptatrien-1-yl)tin

生成物 1

HCID 44264058(S)-N-[[3-[3-fluoro-4-(4-methoxy-5-oxo-1,3,6-cycloheptatrien-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide収率 98%

試薬・触媒・溶媒 3

HCID 23938
Palladium
触媒
HCID 178418476HCID 178418476、化合物触媒
HCID 312751,4-Dioxane溶媒

実験手順

A slurry of (S)-N-[[3-(3-fluoro-4-iodophenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide described above (4.200 g, 11.11 mmol) and trimethyl(4-methoxy-5-oxo-1,3,6-cycloheptatrien-1-yl)tin (4.150 g, 13.88 mmol) in 1,4-dioxane (50 mL) was degassed by repeated evacuation and filling with nitrogen. Bis(triphenylphosphine)palladium(II) chloride (0.545 g, 0.78 mmol) was added, the reaction again degassed, and then the mixture was brought to reflux under nitrogen. After 3 h TLC revealed some of the iodide still remained. Additional tin reagent (0.400 g, 1.34 mmol) and palladium catalyst (0.100 g, 0.14 mmol) were added and the mixture refluxed for 4 h. The reaction mixture was cooled to ambient temperature and concentrated under reduced pressure. The residue was dissolved in 20% methanol/chloroform, filtered through Celite and concentrated in vacuo. The crude solids were triturated with dichloromethane/diethyl ether, the solids filtered, washed with diethyl ether and dried in vacuo to give 4.200 g (98%) of the title compound. The following characteristics were noted:

後処理

  1. customwas degassed
  2. customthe reaction
  3. customagain degassed
  4. temperatureto reflux under nitrogen
  5. temperaturethe mixture refluxed for 4 h
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in 20% methanol/chloroform
  8. filtrationfiltered through Celite
  9. concentrationconcentrated in vacuo
  10. customThe crude solids were triturated with dichloromethane/diethyl ether
  11. filtrationthe solids filtered
  12. washwashed with diethyl ether
  13. customdried in vacuo

出典と根拠

ORDレコード
ord-10386cfd5c7e4577a06b4732876447f0
出典データセット
uspto-grants-1996_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05523403

反応ノート

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