Acetic Acid → HCID 91000778, compound

Participants

Reaction Steps

Acetic acid (0.207 ml) and 1.21 ml of a 1 M tetra-n-butylammonium fluoride/THF solution were added to a solution of 265 mg of 4-nitrobenzyl (1S,5R,6S)-2-[7-(2-t-butyldimethylsilyloxyethyl)thioimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate in 5 ml of THF. The mixture was stirred at room temperature for 6 hr. Brine was added to the reaction solution, and a saturated sodium hydrogencarbonate solution was added thereto. The mixture was adjusted to pH 8.2, and was extracted with ethyl acetate twice. The organic layers were combined, were washed with brine, and were dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=20:1) to prepare 208 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-[7-(2-hydroxyethyl)thioimidazo[5,1-b]thiazol-2-yl]-1-methyl-1-carbapen-2-em-3-carboxylate.

Provenance & Evidence