HCID 19971504, compound → HCID 86750489, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{2-(imidazol-1-yl)ethyl}pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (7.00 g) in dimethylformamide (35 ml) was added 3-allyloxycarbonylamino-l-iodopropane (4.26 g) and the solution was warmed to 50° C. After stirring at the same temperature for 8 hours, the solution was cooled to room temperature. The solvent was evaporated and the residue was washed with diisopropyl ether (175 ml×5) to give allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-[2-[3-{3-(allyloxycarbonylamino)propyl}-1-imidazolio]ethyl]-pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate iodide (10.4 g) as a light brown paste. This compound was immediately used as the starting compound for the next step.

Provenance & Evidence