Methanesulfonyl chloride → HCID 178502810, compound

Participants

Reaction Steps

A stirred solution of 2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetic acid (20.1 mg) and N,N-diisopropylethylamine (0.0176 ml) in dimethylformamide (0.3 ml) was cooled to -55 to -60° C. and methanesulphonyl chloride (0.0081 ml) was added. The mixture was stirred at the same temperature for 0.5 h and then a solution of 4-methoxybenzyl (6R,7R)-7-amino-3-[(2S,5R)-5-methoxy-carbonyltetrahydrofuran-2-yl]ceph-3-em-4-carboxylate (41 mg) in dimethylformamide (0.3 ml) was added followed by pyridine (0.0073 ml). The mixture was then stored at 0° C. for 1 h and then at room temperature for 0.5 h. 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 (31 mg) isolated by column chromatography of the residue (silica gel, ethyl acetate as eluent); νmax (CHCl3) 3496, 3397, 1784, 1733 and 1684 cm-1.

Provenance & Evidence