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项目整合精选>>>Etomoxir, B-8910-02(Na salt), B-877-44, B-80754(racemate), B-82733(racemate, Na salt), B-83721(racemate, free acid)
Etomoxir, B-8910-02(Na salt), B-877-44, B-80754(racemate), B-82733(racemate, Na salt), B-83721(racemate, free acid)
乙莫克舍 乙莫克舍 Chemical Name: (+)-(R)-2-[6-(4-Chlorophenoxy)hexyl]oxirane-2-carboxylic acid ethyl ester
CAS No. 124083-20-1, 82258-36-4 (racemate)
项目整合开发状态: Discontinued
项目研究机构: Altana Pharma (Originator), MediGene (Licensee)
合成路线:1) Alkylation of diethyl malonate (II) with 1 6-dibromohexane (I) results in diethyl 6-bromohexylmaionate (III).Compound (II) is hydrolyzed to the monoester (IV),followed by condensation with paraformaldehyde in ethanol/piperidine/2-methylquinoline to yield ethyl 8-bromo-2-methyleneoctanoate (V),which is oxidized with permaleic acid to (VI).Subsequent reaction with 4-chlorophenolate produces etomoxir.
合成路线:2) Alternatively,etomoxir can be prepared as follows: Alkylation of 4-chlorophenol with 1,6-dibromohexane (I) yields 1 bromo-6-(4-chlorophenoxy)hexane (VII).Diethyl malonate (II) is alkylated by (VII),yielding (VIII),followed by hydrolysis to the monoester (IX),which is condensed with para formaldehyde/pyridine/piperidine to give ethyl 8-(4-chlorophenoxy)-2-methyleneoctanoate (IX).Oxidation with m-chloroperbenzoic acid produces etomoxir.
📌 参考资料/链接：
参考文献标题:Phenoxyalkoxyalkyl- and phenoxyalkyl-substd.oxiranecarboxylic acids,their use and medicaments containing them
文献作者:Eistetter,K.; Ludwig,G.; Rapp,E.; Wolf,H.(Byk Gulden Lomberg Chemische Fabrik GmbH)
参考来源:EP 0046590; US 4337267
📄 详细内容
合成路线:1) Alkylation of diethyl malonate (II) with 1 6-dibromohexane (I) results in diethyl 6-bromohexylmaionate (III).Compound (II) is hydrolyzed to the monoester (IV),followed by condensation with paraformaldehyde in ethanol/piperidine/2-methylquinoline to yield ethyl 8-bromo-2-methyleneoctanoate (V),which is oxidized with permaleic acid to (VI).Subsequent reaction with 4-chlorophenolate produces etomoxir.
合成路线:2) Alternatively,etomoxir can be prepared as follows: Alkylation of 4-chlorophenol with 1,6-dibromohexane (I) yields 1 bromo-6-(4-chlorophenoxy)hexane (VII).Diethyl malonate (II) is alkylated by (VII),yielding (VIII),followed by hydrolysis to the monoester (IX),which is condensed with para formaldehyde/pyridine/piperidine to give ethyl 8-(4-chlorophenoxy)-2-methyleneoctanoate (IX).Oxidation with m-chloroperbenzoic acid produces etomoxir.
参考文献标题:ETOMOXIR
文献作者:Eistetter,K.; Wolf,H.P.O.
参考来源:Drugs Fut 1986,11(12),1034
产品链接: CAS No. 124083-20-1›› 产品链接: CAS No.82258-36-4››