Potassium Bicarbonate → HCID 70480354, compound

Participants

Reaction Steps

To a solution of 350 mg of benzyl (3S, 5R and 3R, 5S)penam-3-carboxylate 1,1-dioxide in 12 ml of methanol was added 75 mg of potassium bicarbonate followed by 350 mg of 10% palladium on carbon. The mixture was shaken under an atmosphere of hydrogen at atmospheric pressure until hydrogen absorption ceased. The catalyst was removed by filtration and then the solvent was removed by evaporation in vacuo. The residue was partitioned between water and ethyl acetate at pH 8. The aqueous layer was removed, and the pH was lowered to 1.5. The acidic aqueous phase was extracted liberally with ethyl acetate. The ethyl acetate extracts were combined, dried (Na2SO4) and concentrated in vacuo. The residue was recrystallized from ethyl acetate-methanol, to give 41 mg of the title compound, mp 164°-167° C. The NMR spectrum (100 MHz; DMSO-d6) showed absorptions at 4.97 (m, 1H), 4.86 (q, 1H), 3.90 (m, 2H) and 3.65 (m, 2H) ppm. The IR spectrum (film) showed absorptions at 1770 and 1725 cm-1. The product had no optical activity.

Provenance & Evidence