Reacción #1551912

Ecuación de reacción

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

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

Disolventes

ethyl acetate

acetone

ethanol

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente