Methanesulfonyl chloride → HCID 172938119, compound

Participants

Reaction Steps

A stirred solution of 2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetic acid (20.1mg) and N,N-diisopropylethylamine (0.0176ml) in dimethylformamide (0.3ml) was cooled to -55 to -60° C. and methanesulphonyl chloride (0.0081ml) was added. The mixture was stirred at the same temperature for 0.5h and then a solution of 4-methoxybenzyl (6R,7R)-7-amino-3-[(2S,5R)-5-methoxycarbonyltetrahydrofuran-2-yl]ceph-3-em-4-carboxylate (41mg) in dimethylformamide (0.3ml) was added followed by pyridine (0.0073ml). The mixture was then stored at 0° C. for 1h and then at room temperature for 0.5h. The reaction mixture was partitioned between ethyl acetate and aqueous citric acid solution and the organic phase washed with water and brine. The solution was dried over magnesium sulphate and evaporated, and the title compound (31mg) isolated by column chromatography of the residue (silica gel, ethyl acetate as eluent); vmax (CHCl3) 3496, 3397, 1784, 1733 and 1684cm-1.

Provenance & Evidence