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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
Notes
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Reaction equation

HRID 259817 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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

Product 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]acetamideYield 98%

Reagents, catalysts & solvents 3

HCID 23938
Palladium
Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 312751,4-DioxaneSolvent

Procedure

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:

Workup

  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

Sources & evidence

ORD record
ord-10386cfd5c7e4577a06b4732876447f0
Source dataset
uspto-grants-1996_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05523403

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes