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项目整合精选>>>Levodropropizine, Levdropropizine, DF-526, Salvituss, Danka, Rapitux, Levotuss
Levodropropizine, Levdropropizine, DF-526, Salvituss, Danka, Rapitux, Levotuss
左羟丙哌嗪 左羟丙哌嗪 Chemical Name: (-)-(S)-3-(4-Phenyl-1-piperazinyl)propane-1,2-diol
CAS No. 99291-25-5, 99291-24-4 ((R)-isomer)
项目整合开发状态: Launched-1989
项目研究机构: Domp?(Originator), Almirall Prodesfarma (Licensee), Angelini (Licensee), Boehringer Ingelheim (Licensee)
合成路线:This compound can be prepared by two related ways:1) The diazotation of L-serine methyl ester (I) with NaNO2 - HCl gives methyl (S)-glycerate (II),which by reaction with 2,2-dimethoxypropane and p-toluenesulfonic acid (or acetone and ZnCl2) is converted to methyl (S)-O-isopropylideneglycerate (III).The reduction of (III) with LiAlH4 in refluxing ether affords (S)-2,3-O-isopropylideneglycerol (IV),which by reaction with tosyl chloride in pyridine is converted to the corresponding tosylate (V).The partial hydrolysis of (V) with HCl in acetone affords (S)-glycerol-1-tosylate (VI),which is finally condensed with 1-phenylpiperazine (VII) in refluxing benzene.2) The partial hydrolysis of (S)-2,3-epoxypropyl tosylate (VIII) with HCl as before gives the glycerol tosylate (VI),already obtained.
📌 参考资料/链接：
参考文献标题:Optically active compounds with antitussive and central sedative activity,a process for the preparation thereof and compositions containing the same
文献作者:Borsa,M.; Tonon,G.; Malandrino,S.(Domp?Farm.SpA)
参考来源:EP 0147847; US 4699911; US 4764515
📄 详细内容
合成路线:This compound can be prepared by two related ways:1) The diazotation of L-serine methyl ester (I) with NaNO2 - HCl gives methyl (S)-glycerate (II),which by reaction with 2,2-dimethoxypropane and p-toluenesulfonic acid (or acetone and ZnCl2) is converted to methyl (S)-O-isopropylideneglycerate (III).The reduction of (III) with LiAlH4 in refluxing ether affords (S)-2,3-O-isopropylideneglycerol (IV),which by reaction with tosyl chloride in pyridine is converted to the corresponding tosylate (V).The partial hydrolysis of (V) with HCl in acetone affords (S)-glycerol-1-tosylate (VI),which is finally condensed with 1-phenylpiperazine (VII) in refluxing benzene.2) The partial hydrolysis of (S)-2,3-epoxypropyl tosylate (VIII) with HCl as before gives the glycerol tosylate (VI),already obtained.
参考文献标题:Synthesis and pharmacological screening of new phenylpiperazinepropane derivatives and their enantiomers
文献作者:Giani,R.; Marione,E.; Melillo,G.; Borsa,M.; Tonon,G.C.
参考来源:Arzneim-Forsch Drug Res 1988,38(8),1139-41
合成路线:This compound can be prepared by two related ways:1) The diazotation of L-serine methyl ester (I) with NaNO2 - HCl gives methyl (S)-glycerate (II),which by reaction with 2,2-dimethoxypropane and p-toluenesulfonic acid (or acetone and ZnCl2) is converted to methyl (S)-O-isopropylideneglycerate (III).The reduction of (III) with LiAlH4 in refluxing ether affords (S)-2,3-O-isopropylideneglycerol (IV),which by reaction with tosyl chloride in pyridine is converted to the corresponding tosylate (V).The partial hydrolysis of (V) with HCl in acetone affords (S)-glycerol-1-tosylate (VI),which is finally condensed with 1-phenylpiperazine (VII) in refluxing benzene.2) The partial hydrolysis of (S)-2,3-epoxypropyl tosylate (VIII) with HCl as before gives the glycerol tosylate (VI),already obtained.
参考文献标题:LEVDROPROPIZINE < Rec INN >
文献作者:Prous,J.; Castar,J.
参考来源:Drugs Fut 1989,14(6),522
产品链接: CAS No. 99291-25-5›› 产品链接: CAS No.99291-24-4››