Acetic Acid → HCID 70150500, compound

Participants

Reaction Steps

To a solution of 799 mg of 4-nitrobenzyl (1S,5R,6S)-2-(5-t-butyldimethylsilyloxymethylimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate in 20 ml of THF were added 1.1 ml of acetic acid and 6.5 ml of 1 M solution of tetra-n-butylammonium fluoride in THF under the atmosphere of argon, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and diluted with 100 ml of ethyl acetate, 100 ml of aqueous saline and a saturated aqueous sodium hydrogen carbonate solution to adjust pH to 7.8. The organic layer was separated, washed with aqueous saline, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by column chromatography on Sephadex LH-20 (chloroform:methanol=1:1) to give 619 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(5-hydroxymethylimidazo[5,1-b]thiazol-2-yl)-1-methyl-1-carbapen-2-em-3-carboxylate.

Provenance & Evidence