Acetic Acid → p-Nitrobenzyl (1RS,5S,6S)-2-phenylthio-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Participants

Reaction Steps

300 μl of acetic acid and 2.1 ml of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran were added to a solution of 298 mg of p-nitrobenzyl (1RS,5S,6S)-2-phenylthio-6-[(1R)-1-t-butyldimethylsilyl-oxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate in 6.4 ml of tetrahydrofuran, kept at 0° to 5° C. with ice-water cooling. The mixture was kept stirred overnight at room temperature, and then for 4 hours in an oil bath at 30° C. The reaction mixture was then diluted with ethyl acetate and washed successively with saturated aqueous sodium chloride solution, 5% aqueous sodium bicarbonate solution, and again saturated aqueous sodium chloride solution. The solvent was distilled off, and the resulting residue was chromatographed on a column of silica gel using a 3/1 mixture of benzene/ethyl acetate as eluent, giving 57 mg of the title compound as pale yellow crystals.

Provenance & Evidence