Triacetoxyperiodinane → HCID 178453955, compound

HRID 1920133Notes

Reaction equation

HRID 1920133 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+]>ClCCl>[C:1]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([CH:14]=[O:15])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 178453956HCID 178453956, compound

Product 1

HCID 178453955HCID 178453955, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane (30 mL) solution of the compound (1.6 g) obtained in Example 22, a Dess-Martin reagent (3.97 g) was added at 0° C. The reaction solution was stirred at room temperature for 16 hours. To the reaction solution, an aqueous saturated sodium hydrogen carbonate solution (50 mL) was added, and then aqueous layer was extracted with dichloromethane. The combined organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. After removing the anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0→8:2) to obtain the title compound (1.60 g) having the following physical properties.

Workup

  1. extractionaqueous layer was extracted with dichloromethane
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing the anhydrous sodium sulfate
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0→8:2)

Sources & evidence

ORD record
ord-3a0e040c8daa472c9990be9eeef40746
Source dataset
uspto-grants-2012_05
Patent number
US08168783B2

Reaction notes

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