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【结 构 式】 
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【分子编号】14893 【品名】N-[[(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]carbonyl]-N,N'-diisopropylurea 【CA登记号】 |
【 分 子 式 】C27H42N2O3 【 分 子 量 】442.64216 【元素组成】C 73.26% H 9.56% N 6.33% O 10.84% |
合成路线1
该中间体在本合成路线中的序号：(IV)2) By the reaction of 3-oxoandrost-4-ene-17beta-carboxylic acid (III) with diisopropylcarbodiimide (II) in refluxing ethyl acetate and subsequent A-ring opening of compound (IV) by treatment with the Lamieux-von Rudloff reagent (permanganate-periodate) in isopropanol. The cyclization of the secoacid (V) so obtained, with methylamine in dioxane under pressure, followed by the hydrogenation under pressure, on 10% Pd/C in ethanol, affords turosteride. This method is used for the large scale production of turosteride.
| 【1】 Panzeri, A.; Di Salle, E.; Nesi, M. (Pharmacia Corp.); 17beta-Substd.-4-aza-5alpha-androstan-3-one derivs. and process for their preparation. EP 0468012; JP 1992505462; US 5155107; WO 9112261 . |
| 【2】 Di Sale, E.; Panzeri, A.; Turosteride. Drugs Fut 1993, 18, 5, 436. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (III) | 14892 | (8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid; 4-Androstene-3-oxo-17-beta-carboxylic acid | 7385-78-6 | C20H28O3 | 详情 | 详情 |
| (IV) | 14893 | N-[[(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]carbonyl]-N,N'-diisopropylurea | C27H42N2O3 | 详情 | 详情 | |
| (V) | 14894 | 3-[(3S,3aS,5aS,6R,9aS,9bS)-3-([isopropyl[(isopropylamino)carbonyl]amino]carbonyl)-3a,6-dimethyl-7-oxododecahydro-1H-cyclopenta[a]naphthalen-6-yl]propionic acid | C26H42N2O5 | 详情 | 详情 | |
| (VI) | 14895 | N-[[(4aR,4bS,6aS,7S,9aS,9bS)-1,4a,6a-trimethyl-2-oxo-2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydro-1H-indeno[5,4-f]quinolin-7-yl]carbonyl]-N,N'-diisopropylurea | C27H43N3O3 | 详情 | 详情 |