新产品编号:2256441
Chemical Name: 3(S)-(3-Fluorophenyl)-3-[2-[2-oxo-3(S)-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]pyrrolidin-1-yl]acetamido]propionic acid
项目整合开发状态: Preclinical
项目研究机构: Merck & Co. (Originator)
合成路线:Ethyl 3-fluorocinnamate (III) was prepared by Wittig condensation of 3-fluorobenzaldehyde (I) with phosphorane (II).Conjugate addition of (R)-N-benzyl-alpha-methylbenzylamine (IV) to the unsaturated ester (III) furnished the chiral amino ester (V).The primary amine (VI) was then obtained by hydrogenolysis of the N-benzyl groups in the presence of palladium hydroxyde.Coupling of the known pyrrolidinoneacetic acid (VII) to the amino ester (VI) by means of EDC/HOBt afforded amide (VIII).Finally,saponification of the ethyl ester group of (VIII) led to the corresponding carboxylic acid.
📌 参考资料/链接：
参考文献标题:Non-peptide alphavbeta3 antagonists.Part 3: Identification of potent RGD mimetics incorporating novel beta-amino acids as aspartic acid replacements
文献作者:Brashear,K.M.; Coleman,P.J.; Hunt,C.A.; Hoffman,W.F.; Hutchinson,J.H.; Breslin,M.J.; McVean,C.A.; Askew,B.C.; Hartman,G.D.; Rodan,S.B.; Rodan,G.A.; Leu,C.T.; Prueksaritanont,T.; Fernandez-Metzler,C.; Ma,B.; Libby,L.A.; et al.
参考来源:Bioorg Med Chem Lett 2002,12(1),31