(2S)-2-amino-5-[[(E)-benzylidene]amino]pentanoic acid -Drug Synthesis Database

【结构式】

【分子编号】17291

【品名】(2S)-2-amino-5-[[(E)-benzylidene]amino]pentanoic acid

【CA登记号】

【分子式】C₁₂H₁₆N₂O₂

【分子量】220.27132

【元素组成】C 65.43% H 7.32% N 12.72% O 14.53%

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：(XIII)

5) The reaction of L-ornithine (III) with benzaldehyde by means of LiOH gives Ndelta-benzylidene-L-ornitine (XIII), which is treated first with benzyl chloroformate and NaOH and hydrolyzed with HCl to afford Nalpha-(benzyloxycarbonyl)-L-ornithine (XIV). The condensation of (XIV) with N,S-dimethylisothiouronium iodide (II) by means of NaOH gives Nalpha-(benzyloxycarbonyl)-Nomega-methyl-L-arginine (XV), which is finally deprotected by hydrogenation with H2 over Pd/C.

参考文献中间体

合成目标

【1】 Sala, A.; Ferrario, F.; Trupiano, F.; Levi, S.; Multigram synthesis of NG-methyl-(L-)-arginine and its analytical characterization. Synth Commun 1991, 21, 99-105.
【2】 Wroblewski, T.; Castañer, J.; Prous, J.R.; 546C88. Drugs Fut 1998, 23, 2, 123.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(II)	17284	(methylamino)(methylsulfanyl)methaniminium iodide		C₃H₉IN₂S	详情	详情
(III)	12034	4-Chlorophenylamine; 4-Chloroaniline; p-Chloroaniline	106-47-8	C₆H₆ClN	详情	详情
(III)	17285	L-ornithine	70-26-8	C₅H₁₂N₂O₂	详情	详情
(XIII)	17291	(2S)-2-amino-5-[[(E)-benzylidene]amino]pentanoic acid		C₁₂H₁₆N₂O₂	详情	详情
(XIV)	17292	(2S)-5-amino-2-[[(benzyloxy)carbonyl]amino]pentanoic acid		C₁₃H₁₈N₂O₄	详情	详情
(XV)	17293	(2S)-2-[[(benzyloxy)carbonyl]amino]-5-[[imino(methylamino)methyl]amino]pentanoic acid		C₁₅H₂₂N₄O₄	详情	详情

Extended Information