LY-178207(free base), GYKI-14451
Chemical Name: tert-Butyloxycarbonyl-D-phenylalanyl-L-prolyl-L-arginine aldehyde sulfate (2:1); (S)-N-[(1,1-Dimethylethoxy)carbonyl]-D-phenylalanyl-N-[4-[(aminoiminoethyl)amino]-1-formylbutyl]-L-prolinamide sulfate (2:1); Boc-D-Phe-Pro-Arg-H sulfate (2:1)
CAS No. 69201-89-4 (free base)
项目整合开发状态: Preclinical
项目研究机构: Gedeon Richter (Originator), Lilly (Originator)
合成路线:N2-tert-Butoxycarbonyl-N6-benzyloxycarbonyl-L-arginine (I) is converted by treatment with isobutyl oxycarbonyl chloride (A) and N-methylmorpholine (B) to the lactam (II),and the tert-butoxycarbonyl group is cleaved off to give the aminolactam (III),which is coupled with N-tert-butoxycarbonyl-D-phenylalanyl-L-proline (IV) to the tripeptide (V) using the mixed anhydride method as in the first step.The lactam carbonyl is reduced with LiAlH4 to an aldehyde group present as the cyclic a aminoalcohol (VI).Removal of the benzyloxycarbonyl blocking group provides GYKI-14451.In solution the aldehyde group is either in the cyclic alpha-aminoalcohol form or is hydrated.
📌 参考资料/链接：
参考文献标题:D-Phenylalanyl-L-prolyl-L-arginine aldehyde sulfate and process for the preparation thereof
文献作者:Bajusz,S.; Szell,E.; Barabas,E.; Bagdy,D.(Gedeon Richter Ltd.)
参考来源:DE 3200812; FR 2497799; GB 2091270; JP 57181046; US 4399065; US 4478745
📄 详细内容
合成路线:N2-tert-Butoxycarbonyl-N6-benzyloxycarbonyl-L-arginine (I) is converted by treatment with isobutyl oxycarbonyl chloride (A) and N-methylmorpholine (B) to the lactam (II),and the tert-butoxycarbonyl group is cleaved off to give the aminolactam (III),which is coupled with N-tert-butoxycarbonyl-D-phenylalanyl-L-proline (IV) to the tripeptide (V) using the mixed anhydride method as in the first step.The lactam carbonyl is reduced with LiAlH4 to an aldehyde group present as the cyclic a aminoalcohol (VI).Removal of the benzyloxycarbonyl blocking group provides GYKI-14451.In solution the aldehyde group is either in the cyclic alpha-aminoalcohol form or is hydrated.
参考文献标题:GYKI-14451
文献作者:N骻r醖i,M.
参考来源:Drugs Fut 1985,10(1),23
合成路线:N2-tert-Butoxycarbonyl-N6-benzyloxycarbonyl-L-arginine (I) is converted by treatment with isobutyl oxycarbonyl chloride (A) and N-methylmorpholine (B) to the lactam (II),and the tert-butoxycarbonyl group is cleaved off to give the aminolactam (III),which is coupled with N-tert-butoxycarbonyl-D-phenylalanyl-L-proline (IV) to the tripeptide (V) using the mixed anhydride method as in the first step.The lactam carbonyl is reduced with LiAlH4 to an aldehyde group present as the cyclic a aminoalcohol (VI).Removal of the benzyloxycarbonyl blocking group provides GYKI-14451.In solution the aldehyde group is either in the cyclic alpha-aminoalcohol form or is hydrated.
参考文献标题:
文献作者:Voutilainen,S.; Valkonen,V.P.; Venho,B.; et al.
参考来源:Magy K閙 Lapja 1982,27(2),358-365
产品链接: CAS No. 69201-89-4››