Methane → SB202235

HRID 1376893Notes

Reaction equation

HRID 1376893 reaction equation
[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][C:12]2[C@H:13]([NH:16][OH:17])[CH2:14][O:15][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N:24]=[C:25]=[O:26])(C)C.CN(C=O)C.C>C1COCC1>[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][C:12]2[C@H:13]([N:16]([OH:17])[C:25]([NH2:24])=[O:26])[CH2:14][O:15][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 6228DimethylformamideHCID 70696Trimethylsilyl isocyanateHCID 11076092HCID 11076092, compound

Product 1

HCID 153939SB202235Yield 70.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 5 L, 3-necked flask equipped with a mechanical stirrer, thermometer and condenser with CaCl2 drying tube was added under a N2 atmosphere (S)-N-[6-benzyloxy-2,3-dihydrobenzofuran-3-yl]hydroxylamine (129.0 g, 0.501 mol) in THF (2.6 L). The resulting mixture was stirred at room temperature for 0.5 h, at which time was added in one portion, trimethylsilylisocyanate (107.2 mL, 86.6 g, 0.752 mol). The mixture was then heated at reflux for 15 min, then was cooled to 5° C. with an ice bath. The precipitate which formed was collected by filtration to afford a white solid. A second crop of peach-colored solid was obtained from concentration of the filtrate. This was taken up in a minimum of DMF, heated and treated with Darco. Filtration and cooling afforded a white solid which was collected, dried and combined with the first crop. The combined solids were dissolved in EtOH (20 vol), heated to reflux, cooled, collected and dried to afford the title compound (105.4 g, 70.2%); m.p. 192.5°-193° C.

Workup

  1. customTo a 5 L, 3-necked flask equipped with a mechanical stirrer
  2. temperatureThe mixture was then heated
  3. temperatureat reflux for 15 min
  4. temperaturewas cooled to 5° C. with an ice bath
  5. customThe precipitate which formed
  6. filtrationwas collected by filtration
  7. customto afford a white solid
  8. customA second crop of peach-colored solid was obtained from concentration of the filtrate
  9. temperatureheated
  10. filtrationFiltration
  11. temperaturecooling
  12. customafforded a white solid which
  13. customwas collected
  14. customdried
  15. dissolutionThe combined solids were dissolved in EtOH (20 vol)
  16. temperatureheated
  17. temperatureto reflux
  18. temperaturecooled
  19. customcollected
  20. customdried

Sources & evidence

ORD record
ord-914b8e9bddd84eee860dd061eeb66ad7
Source dataset
uspto-grants-1997_09
Patent number
US05663368

Reaction notes

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