Water → HCID 70299392, compound

Participants

Reaction Steps

To a solution of 46.8 mg of (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(5-methylimidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylic acid 5 ml of water was added 134 ml of a 0.1 N aqueous sodium hydrogen carbonate solution. The mixture was lyophilized, dissolved in 1 ml of DMF, added with 0.034 ml of pivaloyloxymethyl iodide under the atmosphere of argon at −30° C., and stirred at the same temperature for 1.5 hours. The reaction mixture was diluted with 50 ml of ethyl acetate, and washed with 50 ml of semi-saturated aqueous saline. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to a volume of 1 ml. The residue thus obtained was purified by column chromatography on silica gel (dichloromethane:methanol=20:1) and on Sephadex LH-20(chloroform:methanol=1:1) in this sequence to give 44.5 mg of the title compound.

Provenance & Evidence