Triacetoxyperiodinane → HCID 68814779, compound

HRID 1436701Notes

Reaction equation

HRID 1436701 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:16]=[C:15]([CH:17]([OH:21])[CH:18]([CH3:20])[CH3:19])[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:16]=[C:15]([C:17](=[O:21])[CH:18]([CH3:19])[CH3:20])[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 68816405HCID 68816405, compound

Product 1

HCID 68814779HCID 68814779, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 5-(1-hydroxy-2-methyl-propyl)-N-methyl-N-propyl-isophthalamic acid methyl ester (70 mg, 0.23 mmol) in dichloromethane (3 mL) and add Dess-Martin periodinane (174 mg, 0.41 mmol) at room temperature. Stir the mixture overnight and quench with 10% aqueous sodium bisulfite solution. Extract the organic layer, wash with saturated aqueous sodium chloride solution, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 30:70 ethyl acetate:hexanes) to give the title compound.

Workup

  1. customquench with 10% aqueous sodium bisulfite solution
  2. extractionExtract the organic layer
  3. washwash with saturated aqueous sodium chloride solution
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 30:70 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-12afa3cd1b4d4764908e5f49fda9d0f7
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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