A-160621
Chemical Name: N-(2-Isopropylthiazol-4-ylmethoxycarbonyl)-L-valine N-[3-[4-(1,3-benzodioxol-5-ylmethyl)-2(S)-(tert-butylcarbamoyl)piperazin-1-yl]-1(S)-benzyl-2(R)-hydroxypropyl]amide
项目整合开发状态: Preclinical
项目研究机构: Abbott (Originator)
合成路线:Intermediate (III) was prepared by condensation of epoxide (I) with piperazine (II).After removal of the carbobenzoxy protecting group of (III) by catalytic hydrogenation,the resulting amine (IV) was coupled to the valine derivative (V) using EDC to afford amide (VI).Subsequent cleavage of the Boc protecting group of (VI) under acidic conditions gave (VII),which was finally alkylated with the benzodioxolylmethyl halide (VIII) to provide the target compound.
📌 参考资料/链接：
参考文献标题:Retroviral protease inhibiting cpds.
文献作者:Chen,X.; Mohammadi,F.; Norbeck,D.W.; Kempf,D.J.(Abbott Laboratories Inc.)
参考来源:WO 9959994
📄 详细内容
合成路线:Intermediate (III) was prepared by condensation of epoxide (I) with piperazine (II).After removal of the carbobenzoxy protecting group of (III) by catalytic hydrogenation,the resulting amine (IV) was coupled to the valine derivative (V) using EDC to afford amide (VI).Subsequent cleavage of the Boc protecting group of (VI) under acidic conditions gave (VII),which was finally alkylated with the benzodioxolylmethyl halide (VIII) to provide the target compound.
参考文献标题:Potent piperazine hydroxyethylamine HIV protease inhibitors containing novel P3 ligands
文献作者:Chen,X.; Kempf,D.J.; Sham,H.L.; Green,B.E.; Molla,A.; Korneyeva,M.; Vasavanonda,S.; Wideburg,N.E.; Saldivar,A.; Marsh,K.C.; McDonald,E.; Norbeck,D.W.
参考来源:Bioorg Med Chem Lett 1998,8(24),3531