18-Crown-6 → HCID 58866131, compound

HRID 1354287Notes

Reaction equation

HRID 1354287 reaction equation
[CH2:1]([O:8][C:9]([C@H:11]1[C@@H:16]2[O:17][C:18]([CH3:21])([CH3:20])[O:19][C@@H:15]2[C@@H:14]([OH:22])[CH2:13][N:12]1[S:23]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)(=[O:25])=[O:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[C:49]([O-])(=[O:51])[CH3:50].[Cs+].C1OCCOCCOCCOCCOCCOC1>C(Cl)Cl.N1C=CC=CC=1.C(#N)C.C(OCC)(=O)C.C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]([C@H:11]1[C@@H:16]2[O:17][C:18]([CH3:21])([CH3:20])[O:19][C@@H:15]2[C@H:14]([O:22][C:49](=[O:51])[CH3:50])[CH2:13][N:12]1[S:23]([C:26]1[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=1)(=[O:25])=[O:24])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 2855718-Crown-6HCID 67749Trifluoromethanesulfonic anhydrideHCID 5152919Cesium acetateHCID 58866169HCID 58866169, compound

Product 1

HCID 58866131HCID 58866131, compoundYield 17.7%

Reagents, catalysts & solvents 4

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 21875418Pyridine methylene chlorideSolvent

Conditions

Temperature
-20 °C

Procedure

The above compound (5) (4.1 g) was dissolved in methylene chloride/pyridine (60–10 mL) and trifluoromethanesulfonic anhydride (2.89 mL) was adding under stirring at −20° C., and then the mixture was stirred at the same temperature for 30 minutes. To the reaction solution was added chloroform (50 mL) and, after washing with 1N hydrochloric acid and saline, the solution was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane 1:1) to obtain a compound, which was dissolved in acetonitrile (60 mL) and cesium acetate (1.77 g) and 18-Crown-6 (3.05 g) were added, followed by stirring at room temperature for 2 hours. To the reaction solution was added ethyl acetate (100 mL) and, after washing with saturated saline, the solution was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate:cyclohexane=1:4→1:3) to obtain the titled compound (791 mg) as a syrup.

Workup

  1. stirringthe mixture was stirred at the same temperature for 30 minutes
  2. washafter washing with 1N hydrochloric acid and saline
  3. dry with materialthe solution was dried over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane 1:1)
  6. customto obtain a compound, which
  7. stirringby stirring at room temperature for 2 hours
  8. washafter washing with saturated saline
  9. dry with materialthe solution was dried over magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:cyclohexane=1:4→1:3)

Sources & evidence

ORD record
ord-7685d16da7224c4c972f60a580f53ab0
Source dataset
uspto-grants-2007_05
Patent number
US07223779B2

Reaction notes

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