Iodomethyl pivalate → HCID 12069977, compound

Participants

Reaction Steps

To a suspension of 947 mg of (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-2-yl)-1-methyl-1-carbapen-2-em-3-carboxylic acid in 180 ml of water was added 7.8 ml of 0.1 N aqueous sodium hydrogen carbonate, and the mixture was stirred at room temperature for 2 hours to form a solution, which was then frozen. The frozen solution was dissolved in 12 ml of dry DMF, mixed with 0.36 ml of iodomethyl pivalate under the atmosphere of argon at −30° C., and stirred for 1.5 hours during which the temperature was raised up to −10° C. The reaction mixture was diluted with 100 ml of ethyl acetate, and washed with 100 ml of semi-saturated aqueous saline. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to a total volume of 5 ml. The residue thus obtained was purified by column chromatography on silica gel (chloroform:methanol 10:1) and on Sephadex LH-20 (chloroform:methanol=1:1) in this sequence to give 576 mg of the title compound.

Provenance & Evidence