【结 构 式】 |
【分子编号】23237 【品名】ethyl 4-[2-[(4-hydroxybenzoyl)amino]phenoxy]butanoate 【CA登记号】 |
【 分 子 式 】C19H21NO5 【 分 子 量 】343.37948 【元素组成】C 66.46% H 6.16% N 4.08% O 23.3% |
合成路线1
该中间体在本合成路线中的序号:(VII)Reduction of ketoester (I) with NaBH4 in THF-MeOH afforded diol (II), which was treated with HCl in toluene to give chlorohydrin (III). Benzanilide (VII) was prepared by condensation of acid chloride (IV) with aniline (V), followed by catalytic hydrogenolysis of the resulting benzyl ether (VI). Then, alkylation of phenol (VII) with chloride (III) in the presence of K2CO3 provided ether (VIII). The hydroxyl group of (VIII) was converted to bromide (IX) using CBr4 and this compound was condensed with N-(2-methoxyphenyl)piperazine (X) to produce disubstituted piperazine (XI). The ethyl ester group of (XI) was finally hydrolyzed using KOH in aqueous EtOH.
【1】 Yoshida, K.; Horikoshi, Y.; Eta, M.; Chikazawa, J.; Ogishima, M.; Fukuda, Y.; Sato, H.; Synthesis of benzanilide derivatives as dual actin. Bioorg Med Chem Lett 1998, 8, 21, 2967. |
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) | 23231 | methyl 3-(4-methylphenyl)-3-oxopropanoate | C11H12O3 | 详情 | 详情 | |
(II) | 23232 | 1-(4-methylphenyl)-1,3-propanediol | C10H14O2 | 详情 | 详情 | |
(III) | 23233 | 3-chloro-3-(4-methylphenyl)-1-propanol | C10H13ClO | 详情 | 详情 | |
(IV) | 23234 | 4-(benzyloxy)benzoyl chloride | C14H11ClO2 | 详情 | 详情 | |
(V) | 21940 | ethyl 4-(2-aminophenoxy)butanoate | C12H17NO3 | 详情 | 详情 | |
(VI) | 23236 | ethyl 4-(2-[[4-(benzyloxy)benzoyl]amino]phenoxy)butanoate | C26H27NO5 | 详情 | 详情 | |
(VII) | 23237 | ethyl 4-[2-[(4-hydroxybenzoyl)amino]phenoxy]butanoate | C19H21NO5 | 详情 | 详情 | |
(VIII) | 23238 | ethyl 4-[2-([4-[3-hydroxy-1-(4-methylphenyl)propoxy]benzoyl]amino)phenoxy]butanoate | C29H33NO6 | 详情 | 详情 | |
(IX) | 23239 | ethyl 4-[2-([4-[3-bromo-1-(4-methylphenyl)propoxy]benzoyl]amino)phenoxy]butanoate | C29H32BrNO5 | 详情 | 详情 | |
(X) | 11882 | 1-(2-Methoxyphenyl)piperazine; Methyl 2-piperazinophenyl ether; 1-(2-Methoxyphenyl)-piperazine | 35386-24-4 | C11H16N2O | 详情 | 详情 |
(XI) | 23241 | ethyl 4-[2-([4-[3-[4-(2-methoxyphenyl)-1-piperazinyl]-1-(4-methylphenyl)propoxy]benzoyl]amino)phenoxy]butanoate | C40H47N3O6 | 详情 | 详情 |