【结 构 式】 |
【分子编号】58473 【品名】methyl 2-(4-{4-hydroxy-3-isopropyl-5-[2-(4-nitrophenyl)ethynyl]benzyl}-3,5-dimethylphenoxy)acetate 【CA登记号】 |
【 分 子 式 】C29H29NO6 【 分 子 量 】487.5524 【元素组成】C 71.44% H 6% N 2.87% O 19.69% |
合成路线1
该中间体在本合成路线中的序号:(VIII)Metalation of the biarylmethane derivative (I) by means of butyllithium, followed by iodination with N-iodosuccinimide, leads to aryl iodide (II). After desilylation of (II) using tetrabutylammonium fluoride, the resultant phenolic compound (III) is alkylated with methyl bromoacetate (IV) to produce ether (V). Palladium-catalyzed coupling between aryl iodide (V) and the phenylethynyl boronate reagent (VI) furnishes the diaryl acetylene (VII). The amino group of (VII) is oxidized to the corresponding nitro derivative employing m-chloroperbenzoic acid, and the methoxymethyl protecting group is then removed by acidic hydrolysis to afford (VIII). Finally, methyl ester hydrolysis in (VIII) in the presence of LiOH gives the target carboxylic acid.
【1】 Nguyen, N.-H.; et al.; Rational design and synthesis of a novel thyroid hormone antagonist that blocks coactivator recruitment. J Med Chem 2002, 45, 15, 3310. |
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) | 58467 | (4-{2,6-dimethyl-4-[(triisopropylsilyl)oxy]benzyl}-2-isopropylphenoxy)methyl methyl ether; triisopropyl{4-[3-isopropyl-4-(methoxymethoxy)benzyl]-3,5-dimethylphenoxy}silane | C29H46O3Si | 详情 | 详情 | |
(II) | 58468 | (4-{2,6-dimethyl-4-[(triisopropylsilyl)oxy]benzyl}-2-iodo-6-isopropylphenoxy)methyl methyl ether; {4-[3-iodo-5-isopropyl-4-(methoxymethoxy)benzyl]-3,5-dimethylphenoxy}(triisopropyl)silane | C29H45IO3Si | 详情 | 详情 | |
(III) | 58469 | 4-[3-iodo-5-isopropyl-4-(methoxymethoxy)benzyl]-3,5-dimethylphenol | C20H25IO3 | 详情 | 详情 | |
(IV) | 12309 | methyl 2-bromoacetate; methyl bromoacetate | 96-32-2 | C3H5BrO2 | 详情 | 详情 |
(V) | 58470 | methyl 2-{4-[3-iodo-5-isopropyl-4-(methoxymethoxy)benzyl]-3,5-dimethylphenoxy}acetate | C23H29IO5 | 详情 | 详情 | |
(VI) | 58471 | C17H23BKNO | 详情 | 详情 | ||
(VII) | 58472 | methyl 2-{4-[3-[2-(4-aminophenyl)ethynyl]-5-isopropyl-4-(methoxymethoxy)benzyl]-3,5-dimethylphenoxy}acetate | C31H35NO5 | 详情 | 详情 | |
(VIII) | 58473 | methyl 2-(4-{4-hydroxy-3-isopropyl-5-[2-(4-nitrophenyl)ethynyl]benzyl}-3,5-dimethylphenoxy)acetate | C29H29NO6 | 详情 | 详情 |