Triacetoxyperiodinane → HCID 178519238, compound

HRID 15732Notes

Reaction equation

HRID 15732 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][C:14]3=[N:17][NH:18][CH:19]=[C:13]3[CH:12]2[CH2:20][OH:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH2:16][CH2:15][C:14]3=[N:17][NH:18][CH:19]=[C:13]3[CH:12]2[CH:20]=[O:21])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 178527348HCID 178527348, compound

Product 1

HCID 178519238HCID 178519238, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 78 (0.50 g, 1.5 mmol) was dissolved in CH2Cl2 (5 mL). NaHCO3 (0.3 g, 3.6 mmol) was added, followed by Dess-Martin periodinane (0.78 g, 1.8 mmol). The reaction stirred at room temperature for two hours and was quenched with sat. NaHCO3 (10 mL) and 10% w/v sodium bisulfite (10 mL). The mixture was stirred at room temperature for 30 minutes. The reaction mixture was extracted with CH2Cl2 and the combined organic layers were washed with brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to yield 0.4 g of 79 as a white solid that was used without further purification.

Workup

  1. customwas quenched with sat. NaHCO3 (10 mL) and 10%
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. extractionThe reaction mixture was extracted with CH2Cl2
  4. washthe combined organic layers were washed with brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-53b29a51ccae49489e1545faedee3cbf
Source dataset
uspto-grants-2010_06
Patent number
US07732609B2

Reaction notes

Loading…