methyl 4-{[(2-methoxyphenethyl)amino]methyl}benzoate -Drug Synthesis Database

【结构式】

【分子编号】57676

【品名】methyl 4-{[(2-methoxyphenethyl)amino]methyl}benzoate

【CA登记号】

【分子式】C₁₈H₂₁NO₃

【分子量】299.36968

【元素组成】C 72.22% H 7.07% N 4.68% O 16.03%

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：(IV)

2-Methoxyphenethylamine (I) is condensed with methyl 4-formylbenzoate (II) to form imine (III), which is further reduced to amine (IV) with NaBH4 in MeOH. Alkylation of amine (IV) by ethyl 5-bromovalerate (V) affords the amino diester (VI). Methyl ether cleavage in (VI) by means of BBr3 gives rise to the phenol compound (VII), which is alkylated with 4-(chloromethyl)stilbene (VIII) to yield ether (IX). Catalytic hydrogenation of stilbene (IX) yields the phenethylbenzyl derivative (X). Finally, alkaline hydrolysis of the methyl ester groups of (X) leads to the title dicarboxylic acid.

参考文献中间体

合成目标

【1】 Perzborn, E.; Stasch, J.-P.; Heil, M.; Naab, P.; Dembowsky, K.; Alonso-Alija, C.; Stahl, E.; Pernerstorfer, J.; Flubacher, D.; Wunder, F. (Bayer AG); Novel derivs. of dicarboxylic acid having pharmaceutical properties. DE 19943635; EP 1216225; WO 0119780 .

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)	57674	1-Amino-2-(2-methoxyphenyl)ethane; 2-(2-Aminoethyl)anisole; 2-(2-Methoxyphenyl)ethylamine; 2-Methoxyphenethylamine	2045-79-6	C₉H₁₃NO	详情	详情
(II)	10170	methyl 4-formylbenzoate	1571-08-0	C₉H₈O₃	详情	详情
(III)	57675	methyl 4-{[(2-methoxyphenethyl)imino]methyl}benzoate		C₁₈H₁₉NO₃	详情	详情
(IV)	57676	methyl 4-{[(2-methoxyphenethyl)amino]methyl}benzoate		C₁₈H₂₁NO₃	详情	详情
(V)	37151	ethyl 5-bromopentanoate	14660-52-7	C₇H₁₃BrO₂	详情	详情
(VI)	57677	methyl 4-{[(5-ethoxy-5-oxopentyl)(2-methoxyphenethyl)amino]methyl}benzoate		C₂₅H₃₃NO₅	详情	详情
(VII)	57678	methyl 4-{[(2-hydroxyphenethyl)(5-methoxy-5-oxopentyl)amino]methyl}benzoate		C₂₃H₂₉NO₅	详情	详情
(VIII)	57679	4-Chloromethylstilbene		C₁₅H₁₃Cl	详情	详情
(IX)	57680	methyl 4-({(5-methoxy-5-oxopentyl)[2-({4-[(E)-2-phenylethenyl]benzyl}oxy)phenethyl]amino}methyl)benzoate		C₃₈H₄₁NO₅	详情	详情
(X)	57681	methyl 4-[((5-methoxy-5-oxopentyl){2-[(4-phenethylbenzyl)oxy]phenethyl}amino)methyl]benzoate		C₃₈H₄₃NO₅	详情	详情

Extended Information