(6R,7R)-7-氨基-3-[2-(4-甲基-5-噻唑)乙烯基]-8-氧代-5-硫-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸的合成

以1-磺丁基-3-甲基咪唑硫酸氢盐离子液体(b)为反应介质,7-氨基头孢烷酸(7-ACA,2)为原料,与4-甲基-5-甲酰基噻唑经缩合反应制得(6R,7R)-7-氨基-3-[2-(4-甲基-5-噻唑)乙烯基]-8-氧代-5-硫-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸(7-ATCA,1),其结构经1H NMR,13C NMR和IR表征。考察了离子液体及其用量,原料摩尔比r[n(4-甲基-5-甲酰基噻唑)∶n(2)],反应温度和反应时间对1收率的影响。在最佳反应条件[b为反应介质,b用量为20 m L,r=1.3,于65℃反应5 h]下,1收率可达90%以上。

Synthesis of (6R,7R)-7-Amino-3-[2-(4-methylthiazol-5-yl) vinyl]-3-cephem-4-carboxylic Acid

7-Amino-3-[2-(4-methylthiazol-5-yl) vinyl]-3-cephem-4-carboxylicacid (7-ATCA, 1) was prepared by condensation reaction of 7-aminocephalosporanic acid (7-ACA, 2) with 4-methylthiazole-5-aldehyde using 1-sulfobutyl-3-methyl-imidazolium hydrogen sulfate ( b ) as reaction medium. The structure was confirmed by 1 H NMR, 13 C NMR and IR. The effect of ionic liquid and its dosage, the ratio of the reactants r [ n ( 4-methylthiazole-5-aldehyde ) ∶n ( 2 ) ] , reaction temperature and reaction time on the yield of 1 were studied. In the optimum reaction conditions [ b as reaction medium, the amountof b was 20 mL, r=1. 3, at 65 ℃ for 5 h], the yield of 1 was above 90%.