Phosphate → (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(3-methylimidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylic Acid

Participants

Reaction Steps

To a solution of 157.3 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(3-methylimidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate in 3 ml of THF and 3 ml of {fraction (1/15)} M phosphate buffer (pH 6.8) was added 0.24 g of 100 Pd-C. The reactor was purged with hydrogen, the reaction mixture was stirred at room temperature for 1 hour. The catalyst was collected by filtration, and washed with 50 ml of water. The filtrate was diluted with 20 ml of ethyl acetate, separated, and the organic layer was further washed with water. The combined aqueous layer was concentrated under reduced pressure to a volume of about 30 ml. The residual concentrate was purified by column chromatography on DIAION HP-20. The fraction containing the aimed product was lyophilized to give 63.5 mg of the title compound.

Provenance & Evidence