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【结 构 式】 
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【分子编号】26905 【品名】2-[(2,2-dimethylpropanoyl)amino]-4-isobutylphenylboronic acid 【CA登记号】 |
【 分 子 式 】C15H24BNO3 【 分 子 量 】277.1715 【元素组成】C 65% H 8.73% B 3.9% N 5.05% O 17.32% |
合成路线1
该中间体在本合成路线中的序号：(XVII)In an alternative procedure, Wittig reaction of 3-nitrobenzaldehyde (XI) with isopropyltriphenylphosphonium iodide gave isobutenyl compound (XII). Then, the nitro group of (XII) was selectively reduced to aniline (XIII) by hydrogenation over Pt/C, and this was protected as the pivaloyl amide (XIV) with pivaloyl chloride. Further hydrogenation of (XIV) using Pd/C produced the isobutyl derivative (XV). Lithiation of (XV) with tert-butyllithium generated the intermediate organolithium reagent (XVI), which was subsequently converted to boronic acid (XVII). Further Suzuki coupling of (XVII) with bromosulfonamide (IV) produced biphenyl (XVIII). Reductive removal of the pivaloyl group of (XVIII) using DIBAL-H then gave the precursor (X), which was finally deprotected with HCl to afford the target compound.
| 【1】 Biphenylsulfonamide endothelin antagonists: Structure-activity relationships of a series of mono- and disubstituted analogues and pharmacology of the orally active endothelin antagonist 2'-amino-N-(3,4-dimethyl-5-isoxazolyl)-4'-(2-methylpropyl)[1,1'-biphe. J Med Chem 1998, 41, 26, 5198. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 40672 | isopropyl(triphenyl)phosphonium | C21H22P | 详情 | 详情 | ||
| (IV) | 26893 | 2-bromo-N-(3,4-dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]benzenesulfonamide | C15H19BrN2O5S | 详情 | 详情 | |
| (X) | 26899 | 2'-amino-N-(3,4-dimethyl-5-isoxazolyl)-4'-isobutyl-N-[(2-methoxyethoxy)methyl][1,1'-biphenyl]-2-sulfonamide | C25H33N3O5S | 详情 | 详情 | |
| (XI) | 12646 | 3-Nitrobenzaldehyde | 99-61-6 | C7H5NO3 | 详情 | 详情 |
| (XII) | 26900 | 1-(2-methyl-1-propenyl)-3-nitrobenzene | C10H11NO2 | 详情 | 详情 | |
| (XIII) | 26901 | 3-(2-methyl-1-propenyl)aniline | C10H13N | 详情 | 详情 | |
| (XIV) | 26902 | 2,2-dimethyl-N-[3-(2-methyl-1-propenyl)phenyl]propanamide | C15H21NO | 详情 | 详情 | |
| (XV) | 26903 | N-(3-isobutylphenyl)-2,2-dimethylpropanamide | C15H23NO | 详情 | 详情 | |
| (XVI) | 26904 | [2-[(2,2-dimethylpropanoyl)amino]-4-isobutylphenyl]lithium | C15H22LiNO | 详情 | 详情 | |
| (XVII) | 26905 | 2-[(2,2-dimethylpropanoyl)amino]-4-isobutylphenylboronic acid | C15H24BNO3 | 详情 | 详情 | |
| (XVIII) | 26906 | N-[2'-([(3,4-dimethyl-5-isoxazolyl)[(2-methoxyethoxy)methyl]amino]sulfonyl)-4-isobutyl[1,1'-biphenyl]-2-yl]-2,2-dimethylpropanamide | C30H41N3O6S | 详情 | 详情 |