Hydrogen Peroxide → allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylsulfinyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 1464730Notes

Reaction equation

HRID 1464730 reaction equation
[C:1]([Si:5]([CH3:27])([CH3:26])[O:6][C@@H:7]([C@H:9]1[C:15](=[O:16])[N:14]2[C@@H:10]1[C@@H:11]([CH3:25])[C:12]([S:23][CH3:24])=[C:13]2[C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[OH:28]O>CC(C)=O.C(O)C.C(OCC)(=O)C>[Si:5]([O:6][C@@H:7]([C@H:9]1[C:15](=[O:16])[N:14]2[C@@H:10]1[C@@H:11]([CH3:25])[C:12]([S:23]([CH3:24])=[O:28])=[C:13]2[C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])[CH3:8])([C:1]([CH3:3])([CH3:2])[CH3:4])([CH3:27])[CH3:26]

Participants

6

Reactant 2

HCID 784Hydrogen PeroxideHCID 57185440allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Product 1

HCID 86747784allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylsulfinyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of allyl (4R,5S,6S)-6-[(1R)-1-(tertbutyldimethylsilyloxy)ethyl] -4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (31.4 mg) in a mixture of acetone (1.0 ml) and ethanol (0.1 ml) was added a 30% aqueous solution of hydrogen peroxide (0.2 ml). The reaction was allowed to stand at ambient temperature for 4 days. The mixture was diluted with ethyl acetate, washed with water, 5% aqueous sodium thiosulfate solution, brine, and dried. The solvent was removed off under reduced pressure and the residue was purified by silica gel column chromatography [ethyl acetate-n-hexane (1:3, V/V)] to afford allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylsulfinyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (10.1 mg).

Workup

  1. washwashed with water, 5% aqueous sodium thiosulfate solution, brine
  2. customdried
  3. customThe solvent was removed off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography [ethyl acetate-n-hexane (1:3, V/V)]

Sources & evidence

ORD record
ord-12dbe56dbb5a4d39b789a8b51d5b4261
Source dataset
uspto-grants-1994_04
Patent number
US05306816

Reaction notes

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