Potassium → 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2S,5R,6R)-, 4-oxide

Participants

Reaction Steps

To 50 ml. of water were added 19.4 grams (50 millimoles) of the potassium salt of 6-phenoxyacetamido-2,2-dimethylpenam-3-carboxylic acid. A solution of 20 grams (65 millimoles active oxygen) of Oxone® in 100 ml. water was added dropwise to the penicillin solution over a 45 minute period. The mixture was stirred for about 10 minutes at room temperature. The resulting precipitate was collected by filtration and washed with 25 ml. of water. The precipitate was dried in vacuo at 40° C. overnight to afford 17.95 grams (98%) of the corresponding penicillin sulfoxide. Analysis of the product by high performance liquid chromatography (HPLC) indicated the presence of 23.0% of the α-isomer and 74.1% of the β-isomer.

Provenance & Evidence