Triacetoxyperiodinane → HCID 58424903, compound

HRID 2409423Notes

Reaction equation

HRID 2409423 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:21]=[CH:20][C:7]2[N:8]([CH2:17][O:18][CH3:19])[C:9](=[O:16])[C:10]3[CH:11]=[CH:12][CH:13]=[N:14][C:15]=3[C:6]=2[CH:5]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:19][O:18][CH2:17][N:8]1[C:7]2[CH:20]=[CH:21][C:4]([CH2:3][CH:2]=[O:1])=[CH:5][C:6]=2[C:15]2[N:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]1=[O:16]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 58425007HCID 58425007, compound

Product 1

HCID 58424903HCID 58424903, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (50 mg, 0.18 mmol) prepared in step 4 was dissolved in dichloromethane (10 ml), added with Dess-Martin periodinane (112 mg, 0.26 mmol) at 0° C. The resulting mixture was stirred for 90 minutes at room temperature and poured into saturated sodium bicarbonate aqueous solution. The mixture was extracted with dichloromethane and washed with brine. The organic layer was dried over anhydrous sodium sulfate and concentrated to dryness. The residue was then purified by flash column chromatography (ethylacetate:hexane=1:1) to obtain the title compound (25 mg, yield: 50%, white solid).

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated to dryness
  5. customThe residue was then purified by flash column chromatography (ethylacetate:hexane=1:1)

Sources & evidence

ORD record
ord-9fe14dc9f101499d866cbf67cc7d7353
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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