Chlorotrimethylsilane → HCID 178460196, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-hydroxy-8-carboxy-2(1H)-quinolinone (160 mg) in chloroform (15 ml) was added triethylamine (0.62 ml) and speedily trimethylsilyl chloride (0.57 ml). The mixture was heated to 60° C. for 4 hours, cooled to 0° C. and treated with triethylamine (0.114 ml) and thionyl chloride (0.06 ml), whereupon the resultant solution was stirred for 2 hours at 0° C. and at room temperature for 30 minutes. This solution was added to 3-aminomethyl-7-[2-(2-aminothiazol-4-yl)-2-((Z)-1-carboxy-1-methylethoxyimino)acetamido]ceph-3-em-4-carboxylic acid (360 mg) in methanol (30 ml) containing triethylamine (0.42 ml) at 0° C. The reaction mixture was stirred for 30 minutes at 0° C., stirred for 30 minutes at room temperature, diluted with water, acidified to pH2, concentrated, and purified by chromatography (HP20SS resin eluting with methanol/water/acetic acid) to give the title compound (85 mg); NMR (DMSO-d6 /CD3COOD/CF3COOD) 1.50(s,6H); 3.55(m,2H); 4.40(m,2H); 5.1(d,1H); 5.75(d,1H); 7.00-7.25(,3H); 7.6(d,1H); 7.80(d,1H).

Provenance & Evidence