CGS-13928C
Chemical Name: 1-[N-[1(S)-(Ethoxycarbonyl)-3-phenyl-1S-propyl]alanyl]-2,3-dihydroindole-2(S)-carboxylic acid sodium salt
项目整合开发状态: Biological Testing
项目研究机构: Novartis (Originator)
合成路线:The condensation of ethyl indoline-2-carboxylate (I) with N-benzyloxycarbonylalanine (II) by means of CH2Cl2 gives ethyl N-(benzyloxycarbonylalanyl)indoline-2-carboxylate (III),which is hydrolyzed partially with LiOH in DMF water yielding N-(benzyloxycarbonylalanyl)indoline-2-carboxylic acid (IV).Debenzylation of (IV) by hydrogenation with H2 over Pd/C in aqueous ethanol affords N-alanylindoline-2-carboxylic acid,which is finally reductocondensed with ethyl 2-oxo-3-phenylbutyrate (VI) by means of NaOH and sodium cyanoborohydride or H2 and RaNi in ethanol.
📌 参考资料/链接：
参考文献标题:1-Carboxy-azaalkyl-indolin-2-carboxylic acids,process for preparing them,pharmaceutical compositions containing them and their therapeutical use
文献作者:Renfroe,H.B.; Stanton,J.L.; Sele,A.(Novartis AG)
参考来源:DD 201888; EP 0051301; GB 2086390
📄 详细内容
合成路线:The condensation of ethyl indoline-2-carboxylate (I) with N-benzyloxycarbonylalanine (II) by means of CH2Cl2 gives ethyl N-(benzyloxycarbonylalanyl)indoline-2-carboxylate (III),which is hydrolyzed partially with LiOH in DMF water yielding N-(benzyloxycarbonylalanyl)indoline-2-carboxylic acid (IV).Debenzylation of (IV) by hydrogenation with H2 over Pd/C in aqueous ethanol affords N-alanylindoline-2-carboxylic acid,which is finally reductocondensed with ethyl 2-oxo-3-phenylbutyrate (VI) by means of NaOH and sodium cyanoborohydride or H2 and RaNi in ethanol.
参考文献标题:CGS-13928C
文献作者:Serradell,M.N.; Casta馿r,J.
参考来源:Drugs Fut 1985,10(3),190