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【结 构 式】 
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【分子编号】57681 【品名】methyl 4-[((5-methoxy-5-oxopentyl){2-[(4-phenethylbenzyl)oxy]phenethyl}amino)methyl]benzoate 【CA登记号】 |
【 分 子 式 】C38H43NO5 【 分 子 量 】593.76316 【元素组成】C 76.87% H 7.3% N 2.36% O 13.47% |
合成路线1
该中间体在本合成路线中的序号：(X)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.
| 【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 |