L-054522
N-[4-[(2-氧-2,3-二氢-1h-苯并咪唑-1-基)哌啶-1-酰羰基]-[3(S)-甲基]-D-色氨酸-L-赖氨酸 Tert-丁基酯Chemical Name: N-[4-(2-Oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-ylcarbonyl]-[3(S)-methyl]-D-tryptophyl-L-lysine tert-butyl ester
CAS No. 214348-67-1
项目整合开发状态: Preclinical
项目研究机构: Merck & Co. (Originator)
合成路线:Coupling of N-Boc-beta-methyltryptophan (I) with N-Cbz-lysine tert-butyl ester (II) using EDC and HOBt afforded dipeptide (III).Selective deprotection of the Boc group of (III) with methanesulfonic acid gave amine (IV).This was converted to urea (VI) upon treatment with benzimidazolylpiperidine (V) and N,N'-disuccinimidyl carbonate in the presence of diisopropyl ethylamine.The N-carbobenzoxy group of (VI) was finally deprotected by hydrogenolysis over Pd/C.
📌 参考资料/链接：
参考文献标题:Somatostatin agonists
文献作者:Berk,S.; Yang,L.; Chen,M.H.; Johnston,D.; Pasternak,A.; Chapman,K.; Guo,L.; Nargund,R.; Tata,J.R.; Patchett,A.A.(Merck & Co.,Inc.)
参考来源:EP 0984779; US 6063796; WO 9844922
📄 详细内容
合成路线:Coupling of N-Boc-beta-methyltryptophan (I) with N-Cbz-lysine tert-butyl ester (II) using EDC and HOBt afforded dipeptide (III).Selective deprotection of the Boc group of (III) with methanesulfonic acid gave amine (IV).This was converted to urea (VI) upon treatment with benzimidazolylpiperidine (V) and N,N'-disuccinimidyl carbonate in the presence of diisopropyl ethylamine.The N-carbobenzoxy group of (VI) was finally deprotected by hydrogenolysis over Pd/C.
参考文献标题:Synthesis and biological activities of potent peptidomimetics selective for somatostatin receptor subtype 2
文献作者:Yang,L.; Berk,S.C.; Rohrer,S.P.; Mosley,R.T.; Guo,L.; Underwood,D.J.; Arison,B.H.; Birzin,E.T.; Hayes,E.C.; Mitra,S.W.; Parmar,R.M.; Cheng,K.; Wu,T.J.; Butler,B.S.; Foor,F.; Pasternak,A.; Pan,Y.; Silva,M.; Freidinger,R.M.; et al.
参考来源:Proc Natl Acad Sci USA 1998,95(18),10836
产品链接: CAS No. 214348-67-1››