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【结 构 式】 
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【分子编号】59442 【品名】N-(3-bromopropyl)-N-ethyl-2,4,6-trimethylbenzenesulfonamide 【CA登记号】 |
【 分 子 式 】C14H22BrNO2S 【 分 子 量 】348.30422 【元素组成】C 48.28% H 6.37% Br 22.94% N 4.02% O 9.19% S 9.21% |
合成路线1
该中间体在本合成路线中的序号：(V)The title tetraamino derivative was prepared by two related methods. Conversion of cis-butenediol (I) into the diamine (II) was effected by Mitsunobu condensation of (I) with HN3 with concomitant reduction of the azido group in the presence of PPh3. Acylation of (II) with mesitylenesulfonyl chloride (III) provided the bis-sulfonamide (IV), which was subsequently alkylated with the bromosulfonamide (V) in the presence of NaH to furnish the protected tetraamine (VI). The sulfonamido groups of (VI) were finally hydrolyzed by an HOAc solution of HBr in the presence of phenol.
| 【1】 Witiak, D.T.; Frydman, B.J.; Marton, L.J.; Reddy, V.K.; Valasinas, A.L. (Wisconsin Alumni Research Foundation); Conformationally restricted polyamines and their use as antineoplastic agents. JP 2002508739; WO 9817624 . |
| 【2】 Witiak, D.T.; Frydman, B.J.; Marton, L.J.; Reddy, V.K.; Valasinas, A.L. (Wisconsin Alumni Research Foundation); Conformationally restricted polyamines. US 5889061 . |
| 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) | 36965 | (Z)-2-butene-1,4-diol | 6117-80-2 | C4H8O2 | 详情 | 详情 |
| (II) | 59440 | (Z)-2-butene-1,4-diamine; (Z)-4-amino-2-butenylamine | C4H10N2 | 详情 | 详情 | |
| (III) | 41158 | 2,4,6-trimethylbenzenesulfonyl chloride | 773-64-8 | C9H11ClO2S | 详情 | 详情 |
| (IV) | 59441 | N-{(Z)-4-[(mesitylsulfonyl)amino]-2-butenyl}-2,4,6-trimethylbenzenesulfonamide | C22H30N2O4S2 | 详情 | 详情 | |
| (V) | 59442 | N-(3-bromopropyl)-N-ethyl-2,4,6-trimethylbenzenesulfonamide | C14H22BrNO2S | 详情 | 详情 | |
| (VI) | 59443 | N-{3-[ethyl(mesitylsulfonyl)amino]propyl}-N-{(Z)-4-[{3-[ethyl(mesitylsulfonyl)amino]propyl}(mesitylsulfonyl)amino]-2-butenyl}-2,4,6-trimethylbenzenesulfonamide | C50H72N4O8S4 | 详情 | 详情 |