L-054522-药物合成数据库

【药物名称】L-054522

化学结构式(Chemical Structure):

参考文献No.	37516
标题:	Somatostatin agonists
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.)
来源:	EP 0984779; US 6063796; WO 9844922

合成路线图解说明: 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No.	481474
标题:	Synthesis and biological activities of potent peptidomimetics selective for somatostatin receptor subtype 2
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.
来源:	Proc Natl Acad Sci USA 1998,95(18),10836

合成路线图解说明: 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.