新产品编号:1122147
Chemical Name: (6R,7S)-3-(Acetoxymethyl)-N-(3-iodobenzyl)-7-methoxy-3-cephem-4-carboxamide S,S-dioxide
项目整合开发状态: Biological Testing
项目研究机构: GlaxoSmithKline (Originator)
合成路线:7-Aminocephalosporanic acid (I) was converted to tert-butyl ester (II) by treatment with isobutylene and sulfuric acid.Subsequent diazotization,followed by reaction with methanol and rhodium catalyst,provided the 7-methoxy derivative (IIIa-b) as a diastereomeric mixture.The desired 7S-isomer was then deprotected with trifluoroacetic acid in anisole,yielding carboxylic acid (IV).Coupling of acid (IV) with 3-iodobenzylamine (VI) via activation as the mixed anhydride (V) with ethyl chloroformate gave rise to amide (VII).The sulfide group of (VII) was finally converted into the title sulfone by oxidation with oxone.
📌 参考资料/链接：
参考文献标题:Interleukin converting enzyme and apoptosis
文献作者:Levy,M.A.; Gleason,J.G.(SmithKline Beecham plc)
参考来源:EP 0851760; JP 1999514345; WO 9707805
📄 详细内容
合成路线:The synthesis of the 125I-labeled compound is shown in Scheme 2.Carboxylic acid (IV) was coupled with 3-(tri-n-butylstannyl)benzylamine (VIII) via the mixed anhydride (V) to produce amide (IX).Subsequent oxidation with oxone afforded the sulfone (X).Finally,iododestannylation of (X) employing Na125I and chloramine-T furnished the radiolabeled compound.
参考文献标题:Preparation of 3-125I-benzyl-(6R,7S9-7-methoxy-3-acetoxymethyl-3-cephem-4-carboxamide-1,1-dioxide
文献作者:Garnes,K.T.; et al.
参考来源:J Label Compd Radiopharm 1999,42(1),77