Acetic Acid → allyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-5-yl)-1-methyl-1-carbapen-2-em-3-carboxylate

Participants

Reaction Steps

To a solution of 0.35 g of allyl (1S,5R,6S)-6-((1R)-1-t-butyldimethylsilyloxyethyl)-2-(imidazo[5,1-b]thiazole-5-yl)-1-methyl-1-carbapen-2-em-3-carboxylate in 12 ml of THF was added under ice-cooling 0.66 ml of acetic acid and 2.9 ml of a 1 M solution of tetra-n-butyl-ammonium fluoride in THF, and the mixture was stirred at room temperature for 36 hours. The reaction mixture was diluted with 50 ml of ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous saline in this sequence, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue thus obtained was purified by column chromatography on silica gel (ethyl acetate) to give 0.16 g of allyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-5-yl)-1-methyl-1-carbapen-2-em-3-carboxylate.

Provenance & Evidence