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【结 构 式】

【药物名称】

【化学名称】 

【CA登记号】

【 分 子 式 】C20H26N2O5S

【 分 子 量 】406.50462

【开发单位】

【药理作用】0

合成路线1

Condensation of D-isoleucine (I) with 4-methoxy-benzenesulfonyl chloride (II) in the presence of Et3N afforded sulfonyl derivative (III), which was subsequently converted to tert-butyl ester (V) upon treatment with dimethylformamide di-tert-butyl acetal (IV). Alkylation of (V) with benzyl bromide and K2CO3 in DMF provided the N-benzyl compound (VI). Then, the tert-butyl ester of (VI) was deprotected with HCl in CH2Cl2, and the resulting carboxylic acid (VII) was condensed with O-tert-butyl hydroxylamine using N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide-HCl (EDC) and 1-hydroxybenzotriazole (HOBt) to give the tert-butyl hydroxamate (VIII). The target hydroxamic acid was then obtained by deprotection of (VIII) with HCl in dichloroethane containing one equivalent of EtOH.

1 MacPherson, L.J.; et al.; Discovery of CGS 27023A, a non-peptidic, potent, and orally active stromelysin inhibitor that blocks cartilage degradation in rabbits. J Med Chem 1997, 40, 16, 2525.
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) 21073 (2R,3S)-2-amino-3-methylpentanoic acid C6H13NO2 详情 详情
(II) 15719 4-methoxybenzenesulfonyl chloride 98-68-0 C7H7ClO3S 详情 详情
(III) 21075 (2R,3S)-2-[[(4-methoxyphenyl)sulfonyl]amino]-3-methylpentanoic acid C13H19NO5S 详情 详情
(IV) 21059 N-[di(tert-butoxy)methyl]-N,N-dimethylamine; di(tert-butoxy)-N,N-dimethylmethanamine 36805-97-7 C11H25NO2 详情 详情
(V) 21077 tert-butyl (2R,3S)-2-[[(4-methoxyphenyl)sulfonyl]amino]-3-methylpentanoate C17H27NO5S 详情 详情
(VI) 21078 tert-butyl (2R,3S)-2-[benzyl[(4-methoxyphenyl)sulfonyl]amino]-3-methylpentanoate C24H33NO5S 详情 详情
(VII) 21079 (2R,3S)-2-[benzyl[(4-methoxyphenyl)sulfonyl]amino]-3-methylpentanoic acid C20H25NO5S 详情 详情
(VIII) 21080 (2R,3S)-2-[benzyl[(4-methoxyphenyl)sulfonyl]amino]-N-(tert-butoxy)-3-methylpentanamide C24H34N2O5S 详情 详情
Extended Information