tert-butyl (E)-3-[4-(2-nitriloethyl)phenyl]-2-propenoate -Drug Synthesis Database

【结构式】

【分子编号】62371

【品名】tert-butyl (E)-3-[4-(2-nitriloethyl)phenyl]-2-propenoate

【CA登记号】

【分子式】C₁₅H₁₇NO₂

【分子量】243.30552

【元素组成】C 74.05% H 7.04% N 5.76% O 13.15%

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：(III)

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

Extended Information