Triacetoxyperiodinane → HCID 59167774, compound

HRID 1616539Notes

Reaction equation

HRID 1616539 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][O:24][C:25](=[O:44])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32](=[O:43])[NH:33][CH2:34][CH:35]([OH:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)Cl>[CH3:23][O:24][C:25](=[O:44])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32](=[O:43])[NH:33][CH2:34][C:35](=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57495437HCID 57495437, compound

Product 1

HCID 59167774HCID 59167774, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add Dess-Martin periodinane (16.5 g, 38.7 mmol) to a solution of 7-(2-hydroxy-2-phenylethylcarbamoyl)heptanoic acid methyl ester (10.2 g, 33.3 mmol) in methylene chloride (360 mL) at 0° C. under nitrogen, stir and warm the mixture to room temperature for 4 hours. Filter the mixture through Celite, wash with ethyl acetate (3×100 mL) and remove the solvent under reduced pressure. Purify the residue by flash column chromatography on silica gel, eluting with hexane/ethyl acetate (60:40), to provide 7-(2-oxo-2-phenylethylcarbamoyl)heptanoic acid methyl ester (7.33 g, 72%).

Workup

  1. filtrationFilter the mixture through Celite
  2. washwash with ethyl acetate (3×100 mL)
  3. customremove the solvent under reduced pressure
  4. customPurify the residue by flash column chromatography on silica gel
  5. washeluting with hexane/ethyl acetate (60:40)

Sources & evidence

ORD record
ord-15faa18134fc4722804e5b1e6eb05b77
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

Loading…