Iodomethyl pivalate → HCID 131722913, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 27 mg of sodium (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-7-yl)-1-methyl-1-carbapen-2-em-3-carboxylate in 0.5 ml of DMF was added 4.0 mg of sodium hydrogen carbonate, and the mixture was cooled to −30° C. under the atmosphere of argon. Pivaloyloxymethyl iodide (30 mg) was added, and the reaction mixture was stirred at −20-−30° C. for 1 hour. The reaction mixture was diluted with 20 ml of ethyl acetate and 10 ml of semi-saturated aqueous saline, and the mixture was stirred and separated. The organic layer was washed with semi-saturated aqueous saline, dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure to a volume of about 1 ml. It was purified by column chromatography on silica gel (ethyl acetate-ethyl acetate:methanol=97:3), and the solvent was concentrated under reduced pressure to a volume of about 0.5 ml and added dropwise to isopropyl ether. The resulting precipitate was collected by filtration, and desiccated under reduced pressure to give 17 mg of the title compound.

Provenance & Evidence