tert-butyl 3-[4-(2-aminoethyl)phenyl]propanoate -Drug Synthesis Database

【结构式】

【分子编号】62373

【品名】tert-butyl 3-[4-(2-aminoethyl)phenyl]propanoate

【CA登记号】

【分子式】C₁₅H₂₃NO₂

【分子量】249.35316

【元素组成】C 72.25% H 9.3% N 5.62% O 12.83%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(V)

The intermediate amine (V) was prepared via a Heck reaction between p-bromophenylacetonitrile (I) and tert-butyl acrylate (II) to afford the p-(cyanomethyl)cinnamate (III) . Catalytic double bond hydrogenation in (III) provided the saturated cyano ester (IV), which was then reduced to amine (V) by using NaBH4 in the presence of CoCl2. Alternatively, simultaneous double bond and cyano group reduction was accomplished by hydrogenation of (III) in the presence of Pd/C and HCl.

参考文献中间体

合成目标

【1】 Hutchison, A.J.; Williams, M.; de Jesus, R.; Yokoyama, R.; Oei, H.H.; Ghai, G.R.; Webb, R.L.; Zoganas, H.C.; Stone, G.A.; Jarvis, M.F.; 2-(Arylalkylamino)adenosin-5'-uronamides: A new class of highly selective adenosine A2 receptor ligands. J Med Chem 1990, 33, 7, 1919.

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)	45829	2-(4-bromophenyl)acetonitrile; 4-Bromobenzyl cyanide	16532-79-9	C₈H₆BrN	详情	详情
(II)	12760	tert-butyl acrylate	1663-39-4	C₇H₁₂O₂	详情	详情
(III)	62371	tert-butyl (E)-3-[4-(2-nitriloethyl)phenyl]-2-propenoate		C₁₅H₁₇NO₂	详情	详情
(IV)	62372	tert-butyl 3-[4-(2-nitriloethyl)phenyl]propanoate		C₁₅H₁₉NO₂	详情	详情
(V)	62373	tert-butyl 3-[4-(2-aminoethyl)phenyl]propanoate		C₁₅H₂₃NO₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

Acetonide (VII) was prepared by treatment of 2-chloroadenosine (VI) with 2,2-dimethoxypropane and camphorsulfonic acid. Subsequent oxidation of (VII) with KMnO4 under basic conditions produced the carboxylic acid (VIII). After activation of (VIII) as the corresponding acid chloride (IX), reaction with ethylamine afforded amide (X). Condensation of amine (V) with the chloroadenosine derivative (X) at 130 C furnished the diaminopurine adduct (XI). Finally, simultaneous cleavage of the tert-butyl ester and acetonide groups of (XI) upon acidic treatment provided the title compound

参考文献中间体

合成目标

【1】 Hutchison, A.J.; Williams, M.; de Jesus, R.; Yokoyama, R.; Oei, H.H.; Ghai, G.R.; Webb, R.L.; Zoganas, H.C.; Stone, G.A.; Jarvis, M.F.; 2-(Arylalkylamino)adenosin-5'-uronamides: A new class of highly selective adenosine A2 receptor ligands. J Med Chem 1990, 33, 7, 1919.
【2】 Hutchison, A.J. (Novartis AG); Certain adenosine 5'-carboxamide derivs.. AU 8811233; EP 0277917; JP 1988201196 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(V)	62373	tert-butyl 3-[4-(2-aminoethyl)phenyl]propanoate	C₁₅H₂₃NO₂	详情	详情
(VI)	62374	(2R,3R,4S,5R)-2-(6-amino-2-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol	C₁₀H₁₂ClN₅O₄	详情	详情
(VII)	62375	[(3aR,4R,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methanol	C₁₃H₁₆ClN₅O₄	详情	详情
(VIII)	62376	(3aR,4S,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid	C₁₃H₁₄ClN₅O₅	详情	详情
(IX)	62377	(3aR,4S,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonyl chloride	C₁₃H₁₃Cl₂N₅O₄	详情	详情
(X)	62378	(3aR,4S,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide	C₁₅H₁₉ClN₆O₄	详情	详情
(XI)	62379	tert-butyl 3-(4-{2-[(9-{(3aR,4R,6S,6aR)-6-[(ethylamino)carbonyl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-6-amino-9H-purin-2-yl)amino]ethyl}phenyl)propanoate	C₃₀H₄₁N₇O₆	详情	详情

Extended Information