Sodium Thiosulfate → N-(4-cyanophenyl)-3-methyl-5-oxopentanamide

HRID 2272560Notes

Reaction equation

HRID 2272560 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:17])[CH2:11][CH:12]([CH3:16])[CH2:13][CH2:14][OH:15])=[CH:5][CH:4]=1)#[N:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:17])[CH2:11][CH:12]([CH3:16])[CH2:13][CH:14]=[O:15])=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 86729721N-(4-cyanophenyl)-5-hydroxy-3-methylpentanamide

Product 1

HCID 86729722N-(4-cyanophenyl)-3-methyl-5-oxopentanamideYield 26.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the compound obtained in Step 1 (435 mg, 1.87 mmol) in acetonitrile (10 mL) was added Dess-Martin Periodinane (953 mg, 2.25 mmol), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into aqueous sodium thiosulfate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5 to 80% ethyl acetate/hexane) to give crude N-(4-cyanophenyl)-3-methyl-5-oxopentanamide (113 mg, 0.492 mmol, 26.3%) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 5 to 80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-64d7b4f97f434b2381d3b918e3c34a91
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

Loading…