Acetic Acid → HCID 12069976, compound

Participants

Reaction Steps

To a solution of 111 mg of 4-nitrobenzyl (1S,5R,6S)-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-2-(imidazo[5,1-b]thiazol-2-yl)-1-methyl-1-carbapen-2-em-3-carboxylate in 3 ml of anhydrous THF were added 0.164 ml of acetic acid and 0.954 ml of a 1 M solution of tetra-n-butylammonium fluoride/THF, and the mixture was stirred at room temperature under the atmosphere of argon at 20 hours. The reaction mixture was diluted with ethyl acetate, and washed with a mixed solvent of semi-saturated aqueous saline and saturated aqueous sodium hydrogen carbonate (pH 8.0), and semi-saturated aqueous saline in this sequence. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation. The residue thus obtained was purified by column chromatography on Sephadex LH-20 (chloroform:methanol=1:1) to give 57.3 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-2-yl)-1-methyl-1-carbapen-2-em-3-carboxylate.

Provenance & Evidence