Cefbuperazone sodium, T 1982, BMY-25182, Tomiporan, Keiperazon

头孢拉宗钠 头孢拉宗 Chemical Name: (6R,7S)-7-[(2R,3S)-2-(4-Ethyl-2,3-dioxo-1-piperazinecarboxamido)-3-hydroxybutyramido]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium salt
CAS No. 76648-01-6, 76610-84-9 (free acid)
项目整合开发状态: Launched-1985
项目研究机构: Bristol-Myers Squibb (Originator), Kaken (Originator), Toyama (Originator)
合成路线:The condensation of 4-ethyl-2,3-dioxo-1-piperazinecarbonyl chloride (I) with threonine (II) in methylene chloride gives alpha-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-beta-hydroxybutyric acid (III),which is then condensed with diphenylmethyl 7-beta-amino-3-[(1-methyltetrazol-5-yl)thiometnyl)-Delta3-cephem-4-carboxylate (IV) by means of ethyl chloroformate and N-methyl morpholine yielding diphenylmethyl 7-beta-[alpha-(4-ethyl-2,3-dioxo-1-piperazi-necarboxamido)-beta-hydroxybutyramido]-3-(11-methyltetrazol-5-yl)thiomethyl]-Delta3-cephem-4-carboxylate (V).The methoxylation of (V) with lithium methoxide-methylene chloride THF affords diphenyl methyl 7-beta-[alpha-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-beta-hydroxybutyramido]-7-alpha-methoxy-3-[(1-methyltetrazol-5-yl)thiamethyl-Delta3-cephem-4-carboxylate (VI),which is finally hydrolyzed with trifluoroacetic acid,and treated with NaHCO3 to obtain the sodium salt.