Methyl fluorosulfate → HCID 88417840, compound

Participants

Reaction Steps

90 mg of 4-nitrobenzyl (1R,5S,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-[(2S,4S)-2-(2-trimethylammonioethylcarbamoyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio]-1-carbapen-2-em-3-carboxylate [prepared as described in step (2) above] were dissolved in 2 ml of anhydrous methylene chloride, and the solution was placed on an ice bath. Whilst the solution was still on the ice bath, 20 μl of methyl fluorosulfonate were added, and the resulting mixture was stirred for 30 minutes at room temperature. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting crude product was dissolved in 5 ml of a 1:1 by volume mixture of tetrahydrofuran and water. Hydrogen was passed through the resulting solution for 2 hours at room temperature in the presence of 90 mg of a 10% w/w palladium-on-carbon catalyst. At the end of this time, the catalyst was removed by filtration. The filtrate was condensed by evaporation under reduced pressure, and 5 ml of water were added to the residue. The soluble fraction was subjected to column chromatography through a Sephadex G-10 (Pharmacia, 40-120 μm) column, eluted with water. Those fractions containing the title compound were collected and lyophilized to give 53 mg of the title compound.

Provenance & Evidence