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【结 构 式】 
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【分子编号】44807 【品名】1-(2-ethylbutyl)-N-(2-[[2-([[1-(2-ethylbutyl)cyclohexyl]carbonyl]amino)phenyl]disulfanyl]phenyl)cyclohexanecarboxamide 【CA登记号】 |
【 分 子 式 】C38H56N2O2S2 【 分 子 量 】637.00692 【元素组成】C 71.65% H 8.86% N 4.4% O 5.02% S 10.07% |
合成路线1
该中间体在本合成路线中的序号：(VI)Cyclohexanecarboxylic acid (I) is condensed with 1-bromo-2-ethylbutane (II) by means of lithium diisopropylamide (LDA) (NaH can also be added ) in THF or THF/cyclohexane to afford derivative (III). Treatment of carboxylic acid (III) with oxalyl chloride in CH2Cl2 (a small amount of DMF can be added) yields acid chloride (IV), which is then coupled with bis(2-aminophenyl) disulfide (V) in pyridine to provide disulfide derivative (VI). Reduction of the disulfide bond of (VI) with PPh3 in dioxane/H2O gives benzenethiol (VII), which is finally coupled with isobutyryl chloride (VIII) in pyridine/CHCl3 to furnish the target compound.
| 【2】 Maeda, K.; Okamoto, H.; Shinkai, H. (Japan Tobacco Inc.); CEPT activity inhibitors. EP 1020439; JP 1999049743; JP 1999222428; WO 9835937 . |
| 【1】 maeda, K.; Shinkai, H.; Yamasaki, T.; Okamoto, H.; Uchida, I.; Bis(2-(acylamino)phenyl) disulfides, 2-(acylamino)benzenethiols, and S-(2-(acylamino)phenyl) alkanethioates as novel inhibitors of cholesteryl ester transfer protein. J Med Chem 2000, 43, 19, 3566. |
| 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) | 44803 | cyclohexanecarboxylic acid | 98-89-5 | C7H12O2 | 详情 | 详情 |
| (II) | 44804 | 1-(1-ethylpropyl)-1lambda(3)-dibromane | C5H12Br2 | 详情 | 详情 | |
| (III) | 44805 | 1-(2-ethylbutyl)cyclohexanecarboxylic acid | C13H24O2 | 详情 | 详情 | |
| (IV) | 44806 | 1-(2-ethylbutyl)cyclohexanecarbonyl chloride | C13H23ClO | 详情 | 详情 | |
| (V) | 43460 | 2-[(2-aminophenyl)disulfanyl]aniline; 2-[(2-aminophenyl)disulfanyl]phenylamine | 1141-88-4 | C12H12N2S2 | 详情 | 详情 |
| (VI) | 44807 | 1-(2-ethylbutyl)-N-(2-[[2-([[1-(2-ethylbutyl)cyclohexyl]carbonyl]amino)phenyl]disulfanyl]phenyl)cyclohexanecarboxamide | C38H56N2O2S2 | 详情 | 详情 | |
| (VII) | 44808 | 1-(2-ethylbutyl)-N-(2-sulfanylphenyl)cyclohexanecarboxamide | C19H29NOS | 详情 | 详情 | |
| (VIII) | 14932 | isobutyryl chloride; 2-methylpropanoyl chloride | 79-30-1 | C4H7ClO | 详情 | 详情 |