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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
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HRID 259817 반응식
[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
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참가 물질

7

반응물 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

생성물 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]acetamide수율 98%

시약·촉매·용매 3

HCID 23938
Palladium
촉매
HCID 178418476HCID 178418476, 화합물촉매
HCID 312751,4-Dioxane용매

실험 절차

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:

후처리

  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

출처 및 근거

ORD 기록
ord-10386cfd5c7e4577a06b4732876447f0
출처 데이터셋
uspto-grants-1996_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05523403

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