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【结 构 式】

【分子编号】26904

【品名】[2-[(2,2-dimethylpropanoyl)amino]-4-isobutylphenyl]lithium

【CA登记号】

【 分 子 式 】C15H22LiNO

【 分 子 量 】239.28682

【元素组成】C 75.29% H 9.27% Li 2.9% N 5.85% O 6.69%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XVI)

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
Extended Information