Triacetoxyperiodinane → HCID 86596703, compound

HRID 1269394Notes

Reaction equation

HRID 1269394 reaction equation
[C:1]([O:5][C:6]([NH:8][C@:9]([CH3:31])([CH2:12][CH2:13][C:14]1[O:15][C:16]([C:19](=[O:30])[CH2:20][CH2:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:17][CH:18]=1)[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]([O:5][C:6]([NH:8][C@:9]([CH3:31])([CH2:12][CH2:13][C:14]1[O:15][C:16]([C:19](=[O:30])[CH2:20][CH2:21][CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:17][CH:18]=1)[CH:10]=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66673009HCID 66673009, compound

Product 1

HCID 86596703HCID 86596703, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R)-2-t-butoxycarbonylamino-2-methyl-4-[5-(5-phenylpentanoyl)furan-2-yl]butan-1-ol (110.2 mg, 0.26 mmol) obtained in Example (29a) in dichloromethane (2.6 ml) was added Dess-Martin reagent (165.0 mg, 2.28 mmol), and the resulting mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour. After stirring, the reaction mixture was evaporated in vacuo, and to the residue was added a 10% aqueous sodium thiosulfate solution to decompose the excess reagent. The resulting mixture was extracted with dichloromethane, and the extract was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (3:1) as the eluent to afford the title compound (105.9 mg, yield: 97%).

Workup

  1. stirringAfter stirring
  2. customthe reaction mixture was evaporated in vacuo
  3. additionto the residue was added a 10% aqueous sodium thiosulfate solution
  4. extractionThe resulting mixture was extracted with dichloromethane
  5. washthe extract was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtration
  8. customthe solvent was removed in vacuo
  9. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-5ca91df27e1f43fcb153953666fd5663
Source dataset
uspto-grants-2007_04
Patent number
US07199150B2

Reaction notes

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