2-{(1R,5S)-8-[(2R)-2-amino-5-phenylpentanoyl]-8-azabicyclo[3.2.1]oct-3-yl}-N-ethylbenzamide -Drug Synthesis Database

【结构式】

【分子编号】58375

【品名】2-{(1R,5S)-8-[(2R)-2-amino-5-phenylpentanoyl]-8-azabicyclo[3.2.1]oct-3-yl}-N-ethylbenzamide

【CA登记号】

【分子式】C₂₇H₃₅N₃O₂

【分子量】433.59392

【元素组成】C 74.79% H 8.14% N 9.69% O 7.38%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(XV)

Alkaline hydrolysis of ethyl ester (XII) affords acid (XIII), which is further coupled to ethylamine, producing amide (XIV). Then, removal of the N-Boc group of (XIV) with HCl in EtOAc gives amine (XV). This is coupled to N-Boc-alpha-methylalanine (XVI) to furnish the dipeptide derivative (XVII). Finally, acidic Boc-group cleavage in (XVII) leads to the title compound.

参考文献中间体

合成目标

【1】 Brinkmann, V.; Hesise, C.E.; Davis, M.D.; et al.; FTY720, a novel therapeutic for transplantation and autoimmunity, targets G-protein-coupled receptors for sphingosine-1-phosphate. 19th Int Congr Transplant Soc (Aug 25 2002, Miami) 2002, Abst 0116.
【2】 Patchett, A.A.; Tata, J.R.; Lu, Z. (Merck & Co., Inc.); Bridged piperidines promote release of growth hormone. US 5731317 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XII)	58372	ethyl 2-((1R,5S)-8-{(2R)-2-[(tert-butoxycarbonyl)amino]-5-phenylpentanoyl}-8-azabicyclo[3.2.1]oct-3-yl)benzoate		C₃₂H₄₂N₂O₅	详情	详情
(XIII)	58373	2-((1R,5S)-8-{(2R)-2-[(tert-butoxycarbonyl)amino]-5-phenylpentanoyl}-8-azabicyclo[3.2.1]oct-3-yl)benzoic acid		C₃₀H₃₈N₂O₅	详情	详情
(XIV)	58374	tert-butyl (1R)-1-[((1R,5S)-3-{2-[(ethylamino)carbonyl]phenyl}-8-azabicyclo[3.2.1]oct-8-yl)carbonyl]-4-phenylbutylcarbamate		C₃₂H₄₃N₃O₄	详情	详情
(XV)	58375	2-{(1R,5S)-8-[(2R)-2-amino-5-phenylpentanoyl]-8-azabicyclo[3.2.1]oct-3-yl}-N-ethylbenzamide		C₂₇H₃₅N₃O₂	详情	详情
(XVI)	18471	N-(tert-butoxycarbonyl)-2-methylalanine	30992-29-1	C₉H₁₇NO₄	详情	详情
(XVII)	58376	tert-butyl 2-({(1R)-1-[((1R,5S)-3-{2-[(ethylamino)carbonyl]phenyl}-8-azabicyclo[3.2.1]oct-8-yl)carbonyl]-4-phenylbutyl}amino)-1,1-dimethyl-2-oxoethylcarbamate		C₃₆H₅₀N₄O₅	详情	详情

Extended Information