Boron trifluoride etherate → HCID 68582071, compound

HRID 2234781Notes

Reaction equation

HRID 2234781 reaction equation
C(O[CH:5]1[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@:6]1([CH3:38])[O:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)C.[NH2:39][C:40]1[N:45]=[CH:44][N:43]=[C:42]2[NH:46][N:47]=[C:48]([I:49])[C:41]=12.B(F)(F)F.CCOCC>[N+](C)([O-])=O>[NH2:39][C:40]1[N:45]=[CH:44][N:43]=[C:42]2[N:46]([C@@H:5]3[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:37])[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C@@H:16]([O:17][C:18](=[O:25])[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C@@:6]3([CH3:38])[O:7][C:8](=[O:15])[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:47]=[C:48]([I:49])[C:41]=12

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 68584453HCID 68584453, compoundHCID 178508725HCID 178508725, compound

Product 1

HCID 68582071HCID 68582071, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

1-O-Acetyl-2-C-methyl-2,3,5-tri-O-benzoyl-D-ribofuranose (1.0 g, 1.72 mmol) was dissolved in anhydrous nitromethane (10.0 mL) and to this solution compound 1.2 (312 mg, 1.21 mmol) was added. The resulting suspension was brought to reflux and borontrifluoride etherate (0.23 mL, 1.78 mmol) was added. The suspension became a clear solution, which was heated at reflux for 2 hr. The mixture was cooled, the solvents were evaporated and the off-white foamy residue was dissolved in ethyl acetate and then poured with stirring into aq. sat. NaHCO3. The aqueous layer was extracted twice with ethyl acetate and the combined organic layers were dried (Na2SO4), filtered and evaporated to give an off-white solid. This material was purified by flash column chromatography on silica gel using CH2Cl2 to 2-3% MeOH in dichoromethane as eluent to give the desired compound 1.4 (811 mg) as a yellow foam.

Workup

  1. additionwas added
  2. temperatureto reflux
  3. temperaturewas heated
  4. temperatureat reflux for 2 hr
  5. temperatureThe mixture was cooled
  6. customthe solvents were evaporated
  7. dissolutionthe off-white foamy residue was dissolved in ethyl acetate
  8. additionpoured
  9. extractionThe aqueous layer was extracted twice with ethyl acetate
  10. dry with materialthe combined organic layers were dried (Na2SO4)
  11. filtrationfiltered
  12. customevaporated
  13. customto give an off-white solid
  14. customThis material was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-da8522a348804dc7a1d107ea67b6a53c
Source dataset
uspto-grants-2010_05
Patent number
US07713941B2

Reaction notes

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