Triacetoxyperiodinane → HCID 68814362, compound

HRID 732569Notes

Reaction equation

HRID 732569 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:17]=[C:16]([CH:18]([OH:23])[C:19]([F:22])([F:21])[F:20])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:17]=[C:16]([C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 68814927HCID 68814927, compound

Product 1

HCID 68814362HCID 68814362, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treat a solution of N-methyl-N-propyl-5-(2,2,2-trifluoro-1-hydroxyethyl)-isophthalamic acid ethyl ester (1.8 mmol) in dichloromethane (20 mL) with Dess-Martin reagent at room temperature for 2 h. Quench with 10% aqueous sodium sulfite and extract with ethyl acetate (100 mL). Wash the organic layer with 10% aqueous sodium sulfite, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 60:40 ethyl acetate:hexanes) to give the title compound (330 mg) which is contaminated with recovered N-methyl-N-propyl-5-(2,2,2-trifluoro-1-hydroxyethyl)-isophthalamic acid ethyl ester in a ratio of about 4:1).

Workup

  1. customQuench with 10% aqueous sodium sulfite
  2. extractionextract with ethyl acetate (100 mL)
  3. washWash the organic layer with 10% aqueous sodium sulfite, saturated aqueous sodium chloride
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 60:40 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-31cfb55e5425473eb9d19f7d31b880c3
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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