Remoxipride, FLA-731, A-33547, Roxiam
瑞莫必利Chemical Name: (-)-(S)-3-Bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2,6-dimethoxybenzamide
CAS No. 80125-14-0, 82935-42-0 (HCl)
项目整合开发状态: Launched-1990
项目研究机构: AstraZeneca (Originator), Bracco (Licensee)
合成路线:The bromination of 2,6-dimethoxybenzoic acid (I) with Br2 in dioxane gives 3-bromo-2,6-dimethoxy benzoic acid (II),which is treated with refluxing SOCl2 yielding the corresponding acyl chloride (III).Finally,this compound is condensed with (-)-(S)-1-ethyl 2-(aminomethyl)pyrrolidine (IV).
📌 参考资料/链接：
参考文献标题:Remoxipride
文献作者:Prous,J.; Castar,J.
参考来源:Drugs Fut 1986,11(11),944
📄 详细内容
合成路线:The reaction of N-benzltoxycarbonyl-L-alanine succinimidyl ester (I) with o-glutamine (II) by means of triethylamine in THF water gives benzyloxycarbonyl-L-alanyl-o-glutamine (III),which is esterified with bromobutane and Cs2CO3 in DMF yielding the corresponding butyl ester (IV).Deprotection of (IV) by hydrogenation with H2 over Pd/C in acetic acid affords L-alanyl-D-glutamine n-butyl ester (V),which is condensed with 1-O-benzyl-4,6-O-benzylidene-N-acetylmuramic acid (VI) bv the mixed anhydride method affording 1-O-benzyl-4,6-O-benzylidene-N-acetylmuramyl-L-alanyl-o-glutamine n-butyl ester (VII).Finally,this compound is deprotected by hydrogenation with H2 over Pd/C as before.
合成路线:The bromination of 2,6-dimethoxybenzoic acid (I) with Br2 in dioxane gives 3-bromo-2,6-dimethoxy benzoic acid (II),which is treated with refluxing SOCl2 yielding the corresponding acyl chloride (III).Finally,this compound is condensed with (-)-(S)-1-ethyl 2-(aminomethyl)pyrrolidine (IV).
参考文献标题:Potential neuroleptic agents.2,6-dialkoxybenzamide derivatives with potent dopamine receptor blocking activities
文献作者:Florvall,L.; Ogren,S.O.
参考来源:J Med Chem 1982,25(11),1280
产品链接: CAS No. 80125-14-0›› 产品链接: CAS No.82935-42-0››