(2S)-5-[[amino(imino)methyl]amino]-2-[[(benzyloxy)carbonyl]amino]pentanoic acid -Drug Synthesis Database

【结构式】

【分子编号】37028

【品名】(2S)-5-[[amino(imino)methyl]amino]-2-[[(benzyloxy)carbonyl]amino]pentanoic acid

【CA登记号】

【分子式】C₁₄H₂₀N₄O₄

【分子量】308.33736

【元素组成】C 54.54% H 6.54% N 18.17% O 20.76%

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：(VII)

The condensation of ethyl allophanate (I) with diphenylhydrazine (II) produced 1,2-diphenylurazole (III). Alkylation of (III) with N-(2-bromoethyl)phthalimide (IV) in the presence of potassium tert-butoxide afforded the 4-(2-phthalimidoethyl)urazole (V), and the subsequent hydrazinolysis of the phthalimide group of (V) yielded the amino derivative (VI). Then, coupling of (VI) with N-(benzyloxycarbonyl)arginine (VII) via activation with 1,1'-carbonyldiimidazole (CDI) furnished amide (VIII). Deprotection of the N-benzyloxycarbonyl group of (VIII) to give (IX) was effected by catalytic hydrogenation over Pd/C.

参考文献中间体

合成目标

【1】 Gaida, W.; Schnorrenberg, G.; Dollinger, H.; Doods, H.N.; Esser, F.; Rudolf, K.; Mihm, G. (Boehringer Ingelheim Pharma KG); Novel substd. amino acid derivs., process for their preparation and pharmaceutical compsns. containing them. DE 19816929 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	37022	ethyl aminocarbonylcarbamate	626-36-8	C₄H₈N₂O₃	详情	详情
(II)	37023	1,2-diphenylhydrazine	122-66-7	C₁₂H₁₂N₂	详情	详情
(III)	37024	1,2-diphenyl-1,2,4-triazolidine-3,5-dione		C₁₄H₁₁N₃O₂	详情	详情
(IV)	37025	2-(2-bromoethyl)-1H-isoindole-1,3(2H)-dione	574-98-1	C₁₀H₈BrNO₂	详情	详情
(V)	37026	2-[2-(3,5-dioxo-1,2-diphenyl-1,2,4-triazolidin-4-yl)ethyl]-1H-isoindole-1,3(2H)-dione		C₂₄H₁₈N₄O₄	详情	详情
(VI)	37027	4-(2-aminoethyl)-1,2-diphenyl-1,2,4-triazolidine-3,5-dione		C₁₆H₁₆N₄O₂	详情	详情
(VII)	37028	(2S)-5-[[amino(imino)methyl]amino]-2-[[(benzyloxy)carbonyl]amino]pentanoic acid		C₁₄H₂₀N₄O₄	详情	详情
(VIII)	37029	benzyl (1S)-4-[[amino(imino)methyl]amino]-1-([[2-(3,5-dioxo-1,2-diphenyl-1,2,4-triazolidin-4-yl)ethyl]amino]carbonyl)butylcarbamate		C₃₀H₃₄N₈O₅	详情	详情
(IX)	37030	(2S)-2-amino-5-[[amino(imino)methyl]amino]-N-[2-(3,5-dioxo-1,2-diphenyl-1,2,4-triazolidin-4-yl)ethyl]pentanamide		C₂₂H₂₈N₈O₃	详情	详情

Extended Information