Dichloromethane → HCID 86750491, compound

Participants

Reaction Steps

To a solution of allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{2-(4-carbamoylimidazol-1-yl)ethyl}-pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (2.07 g) in dichloromethane (20 ml) was added methyl trifluoromethanesulfonate (1.16 ml) at 0° C. and the solution was stirred for 30 minutes. To the mixture was added a suspension of ion exchange resin, Amberlist A-26 (Cl- type, Trademark, made by Rohm and Haas Co., Ltd.) (10 ml) in dichloromethane (10 ml) and the whole was stirred for 5 minutes. The resin was removed by filtration and washed with a mixture of dichloromethane and methanol (4/1, 50 ml). The filtrate was concentrated in vacuo to give allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{2-(4-carbamoyl-3-methyl-1-imidazolio)ethyl}pyrrolidin-4yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1azabicyclo[3.2.0]hept-2-ene-2-carboxylate chloride (2.75 g) as a pale yellow solid. This compound was immediately used as the starting compound for the next step.

Provenance & Evidence