Tetrabutylammonium Fluoride → allyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-7-yl)-1-methyl-1-carbapen-2-em-3-carboxylate

Participants

Reaction Steps

To a solution of 460 mg of allyl (1S,5R,6S)-6-((1R)-1-t-butyldimethylsilyloxyethyl)-2-(imidazo[5,1-b]thiazol-7-yl)-1-methyl-1-carbapen-2-em-3-carboxylate in 14 ml of THF were added 860 μl and 3.76 ml of a 1 M tetra-n-butylammonium fluoride in THF, and the mixture was stirred at room temperature for 2 days. The reaction mixture was diluted with 120 ml of ethy acetate, washed with 30 ml of semi-saturated aqueous saline, and then with 30 ml of a mixed solution of semi-saturated aqueous saline and a saturated aqueous sodium hydrogen carbonate solution (1:1), dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by column chromatography on silica gel (dichloromethane:methanol=97:3-95:5) to give 286 mg of allyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-7-yl)-1-methyl-1-carbapen-2-em-3-carboxylate.

Provenance & Evidence