Acetic Acid → HCID 13065657, compound

Participants

Reaction Steps

Pivaloyloxymethyl 2-methyl-1-oxocarbapen-2-em-3-carboxylate, freshly prepared from 50 mg. of pivaloyloxymethyl 1-beta-oxo-2-diazo-3-methylceph-3-em-4-carboxylate by the method of Example 1 (employing the alternative Raney nickel step), was taken up in approximately 0.25 ml. of tetrahydrofuran and added to a slurry of 500 mg. of zinc powder, specially activated by the method of Rieke and Uhm [Synthesis, 452 (1975)], in 15 ml. of acetic acid-30% tetrahydrofuran at 0° C. After stirring for 1 hour at this temperature, the reaction mixture was diluted with toluene, stripped in vacuo and the residue chased several times with toluene. The vacuum pumped residue was taken up in excess methylene chloride, the zinc removed by filtration, and the filtrate reevaporated in vacuo to yield essentially homogeneous pivaloyloxymethyl 2-methyl-1-oxocarbapenam-3-carboxylate (tlc: Rf 0.45 with 18:1 chloroform:ethyl acetate as eluant; ir 1780, 1760 cm-1).

Provenance & Evidence