Vinconate, OM-853(HCl), OC-340, Brenal
长春考酯Chemical Name: (?-3-Ethyl-2,3,a,4-tetrahydro-1H-indolo[3,2,1-de][1,5]naphthyridine-6-carboxylic acid methyl ester
CAS No. 70704-03-9, 70704-04-0 (HCl)
项目整合开发状态: Phase III
项目研究机构: OmniChem (Originator), Mitsubishi Pharma (Licensee)
合成路线:The reaction of methyl-2-oxoglutarate (I) with triethyl orthoformate (A) by means of H2SO4 in refluxing methanol gives methyl 2,2-diethoxyglutarate (II),which is hydrolyzed partially with NaOH in water yielding methyl 2,2-diethoxy-4-carboxybutanoate (III).The reduction of (III) with NaBH4 and BF3 ethearate affords methyl 5-hydroxy-2-oxopentanoate (IV).The controlled oxidation of (IV) with pyridinium chlorochromate and sodium acetate in methylene chloride gives methyl 2,5-dioxopentanoate (V),which is condensed with N-ethyltryptamine (VI) by means of acetic acid in refluxing benzene yielding the tricyclic ketoester (VII).Finally,this compound cyclizes again spontaneously.
📌 参考资料/链接：
参考文献标题:Indole derivatives and therapeutically acting drugs
文献作者:Hannart,J.A.A.J.(OmniChem)
参考来源:BE 0870887; DE 2842418; FR 2404639; GB 2005267; JP 7988300; JP 8331352; US 4200638
📄 详细内容
合成路线:The reaction of methyl-2-oxoglutarate (I) with triethyl orthoformate (A) by means of H2SO4 in refluxing methanol gives methyl 2,2-diethoxyglutarate (II),which is hydrolyzed partially with NaOH in water yielding methyl 2,2-diethoxy-4-carboxybutanoate (III).The reduction of (III) with NaBH4 and BF3 ethearate affords methyl 5-hydroxy-2-oxopentanoate (IV).The controlled oxidation of (IV) with pyridinium chlorochromate and sodium acetate in methylene chloride gives methyl 2,5-dioxopentanoate (V),which is condensed with N-ethyltryptamine (VI) by means of acetic acid in refluxing benzene yielding the tricyclic ketoester (VII).Finally,this compound cyclizes again spontaneously.
参考文献标题:Vinconate
文献作者:Castar,J.; Serradell,M.N.
参考来源:Drugs Fut 1984,9(4),283
产品链接: CAS No. 70704-03-9››