ethyl 3-amino-2-(3,5-dimethoxyphenyl)propanoate -Drug Synthesis Database

【结构式】

【分子编号】46959

【品名】ethyl 3-amino-2-(3,5-dimethoxyphenyl)propanoate

【CA登记号】

【分子式】C₁₃H₁₉NO₄

【分子量】253.2982

【元素组成】C 61.64% H 7.56% N 5.53% O 25.27%

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：(I)

Acylation of ethyl 3-amino-2-(3,5-dimethoxyphenyl)propionate (I) with N-phthaloylglycine (II) using EDC and HOAt afforded amide (III), which was subjected to a Bischler-Napieralski cyclization in the presence of POCl3 to produce the dihydroisoquinoline (IV). Aromatization of (IV) to the corresponding isoquinoline (V) was achieved by treatment with MnO2 in refluxing benzene. Hydrazinolysis of the phthaloyl group of (V) gave the free amine, which was purified after conversion to the N-Boc derivative (VI). Acid cleavage of the Boc group then furnished the title product.

参考文献中间体

合成目标

【1】 Coppola, G.M.; et al.; 1-Aminomethylisoquinoline-4-carboxylates as novel dipeptidylpeptidase IV inhibitors. Bioorg Med Chem Lett 2000, 10, 14, 1555.

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)	46959	ethyl 3-amino-2-(3,5-dimethoxyphenyl)propanoate		C₁₃H₁₉NO₄	详情	详情
(II)	10284	N-Phthaloylglycine; 2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)acetic acid	4702-13-0	C₁₀H₇NO₄	详情	详情
(III)	46960	ethyl 2-(3,5-dimethoxyphenyl)-3-[[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl]amino]propanoate		C₂₃H₂₄N₂O₇	详情	详情
(IV)	46961	ethyl 1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-6,8-dimethoxy-3,4-dihydro-4-isoquinolinecarboxylate		C₂₃H₂₂N₂O₆	详情	详情
(V)	46962	ethyl 1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-6,8-dimethoxy-4-isoquinolinecarboxylate		C₂₃H₂₀N₂O₆	详情	详情
(VI)	46963	ethyl 1-[[(tert-butoxycarbonyl)amino]methyl]-6,8-dimethoxy-4-isoquinolinecarboxylate		C₂₀H₂₆N₂O₆	详情	详情

Extended Information