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【结 构 式】 
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【分子编号】30561 【品名】ethyl 2-(5-bromopentyl)-1,3-dithiane-2-carboxylate 【CA登记号】 |
【 分 子 式 】C12H21BrO2S2 【 分 子 量 】341.33354 【元素组成】C 42.23% H 6.2% Br 23.41% O 9.37% S 18.79% |
合成路线1
该中间体在本合成路线中的序号：(III)The alkylation of ethyl 1,3-dithiane-2-carboxylate (I) with 1,5-dibromopentane (II) by means of NaH in DMF gives ethyl 2-(5-bromopentyl)-1,3-dithiane-2-carboxylate (III), which is treated with NBS in acetonitrile water to open the dithiane ring yielding ethyl 7-bromo-2-oxoheptanoate (IV). Hydrolysis of the ester group of (IV) with 50% HBr affords 7-bromo-2-oxoheptanoic acid (V), which is condensed with 2,2-dimethylcyclopropanecarboxamide (VI) in refluxing toluene giving 7-bromo-2-(2,2-dimethycyclopropanecarboxamido)-2-octenoic acid (VII). Finally, this compound is condensed with L-cysteine (VIII) by means of NaOH in water.
| 【1】 Graham, D.W.; Rogers, E.F.; Kahan, F.M. (Merck & Co., Inc.); 2-(Cyclopropanecarboxamido)-alkenoic acids, their esters and salts, and antibacterial compositions comprising the same a thiennamycin-type compound. EP 0048301 . |
| 【2】 Castaner, J.; Serradell, M.N.; Cilastatin. Drugs Fut 1984, 9, 5, 320. |
| 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) | 30559 | ethyl 1,3-dithiane-2-carboxylate | 20462-00-4 | C7H12O2S2 | 详情 | 详情 |
| (II) | 30560 | 1,5-dibromopentane | 111-24-0 | C5H10Br2 | 详情 | 详情 |
| (III) | 30561 | ethyl 2-(5-bromopentyl)-1,3-dithiane-2-carboxylate | C12H21BrO2S2 | 详情 | 详情 | |
| (IV) | 30562 | ethyl 7-bromo-2-oxoheptanoate | C9H15BrO3 | 详情 | 详情 | |
| (V) | 30563 | 7-bromo-2-oxoheptanoic acid | C7H11BrO3 | 详情 | 详情 | |
| (VI) | 30564 | 2,2-dimethylcyclopropanecarboxamide | C6H11NO | 详情 | 详情 | |
| (VII) | 30565 | (Z)-7-bromo-2-[[(2,2-dimethylcyclopropyl)carbonyl]amino]-2-heptenoic acid | C13H20BrNO3 | 详情 | 详情 | |
| (VIII) | 14643 | L-cysteine; (R)-2-Amino-3-mercaptopropionic acid | 52-90-4 | C3H7NO2S | 详情 | 详情 |