新产品编号:452961
Chemical Name: N-(3,5-Dichlorophenylsulfonyl)-2-methyl-L-prolyl-L-phenylalanine
CAS No. 217452-76-1
项目整合开发状态: Preclinical
项目研究机构: Merck & Co. (Originator)
合成路线:N-Boc-L-Phenylalanine (I) is converted into the tert-butyl ester (II) upon treatment with tert-butyl trichloroacetimidate and boron trifluoride.Then,selective removal of the N-Boc group of (II) with HCl in EtOAc provides L-phenylalanine ester (III).Coupling of (III) with N-Cbz-2-methylproline (IV) furnishes dipeptide (V).After hydrogenolysis of the N-Cbz group of (V),the resultant amine (VI) is acylated by means of 3,5-dichlorobenzenesulfonyl chloride (VII),yielding sulfonamide (VIII).The tert-butyl ester group of (VIII) is finally cleaved by treatment with trifluoroacetic acid in CH2Cl2
📌 参考资料/链接：
参考文献标题:Heterocyclic amide cpds.as cell adhesion inhibitors
文献作者:Hagmann,W.K.; Durette,P.L.; Mumford,R.A.; Mills,S.G.; Kevin,N.J.; Schmidt,J.A.; MacCoss,M.; Van Riper,G.M.(Merck & Co.,Inc.)
参考来源:EP 1001764; WO 9853814
📄 详细内容
合成路线:In an alternative method,L-phenylalanine (I) is esterified employing SOCl2 in MeOH.The resultant phenylalanine methyl ester (II) is then acylated with the sulfonyl proline derivative (III) by means of PyBOP to furnish the sulfonyl dipeptide (IV).Finally,saponification of the methyl ester group of (IV) with LiOH leads to the title compound
参考文献标题:Substituted N-(3,5-dichlorobenzenesulfonyl)-L-prolyl-phenylalanine analogues as potent VLA-4 antagonists
文献作者:Kopka,I.E.; Young,D.N.; Lin,L.S.; Mumford,R.A.; Magriotis,P.A.; MacCoss,M.; Mills,S.G.; Van Riper,G.; McCauley,E.; Egger,L.E.; Kidambi,U.; Schmidt,J.A.; Lyons,K.A.; Stearns,R.A.; Vincent,S.H.; Colletti,A.; Wang,Z.; Tong,S.; et al.
参考来源:Bioorg Med Chem Lett 2002,12(4),637
产品链接: CAS No. 217452-76-1››