• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【药物名称】

【化学名称】 

【CA登记号】

【 分 子 式 】C18H23N3O5S

【 分 子 量 】393.46511

【开发单位】

【药理作用】0

合成路线1

Condensation of D-valine (I) with 4-methoxybenzenesulfonyl 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 2-picolyl chloride-HCl (VI) and K2CO3 in DMF provided the N-(2-picolyl) compound (VII). Then, the tert-butyl ester of (VII) was deprotected with HCl in CH2Cl2, and the resulting carboxylic acid (VIII) was condensed with O-tert-butyl hydroxylamine using N-(3-dimethylaminopropyl)-N'-ethylcarbo-diimide-HCl (EDC) and 1-hydroxybenzotriazole (HOBt) to give the tert-butyl hydroxamate (IX). The target hydroxamic acid was then obtained by deprotection of (IX) 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.
2 MacPherson, L.J.; Parker, D.T.; Jeng, A.Y. (Novartis Corp.); Arylsulfonamido-substd. hydroxamic acids. US 5506242; US 5552419 .
3 MacPherson, L.J.; Parker, D.T. (Novartis Corp.); Arylsulfonamido-substd. hydroxamic acids. US 5646167 .
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) 21056 (R)-(-)-Valine; D-Valine; (R)-alpha-Aminoisovaleric acid 640-68-6 C5H11NO2 详情 详情
(II) 15719 4-methoxybenzenesulfonyl chloride 98-68-0 C7H7ClO3S 详情 详情
(III) 21058 (2R)-2-[[(4-methoxyphenyl)sulfonyl]amino]-3-methylbutyric acid C12H17NO5S 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) 21060 tert-butyl (2R)-2-[[(4-methoxyphenyl)sulfonyl]amino]-3-methylbutanoate C16H25NO5S 详情 详情
(VI) 21061 2-(chloromethyl)pyridine hydrochloride 6959-47-3 C6H7Cl2N 详情 详情
(VII) 21062 tert-butyl (2R)-2-[[(4-methoxyphenyl)sulfonyl](2-pyridinylmethyl)amino]-3-methylbutanoate C22H30N2O5S 详情 详情
(VIII) 21063 (2R)-2-[[(4-methoxyphenyl)sulfonyl](2-pyridinylmethyl)amino]-3-methylbutyric acid hydrochloride C18H23ClN2O5S 详情 详情
(IX) 21064 (2R)-N-(tert-butoxy)-2-[[(4-methoxyphenyl)sulfonyl](2-pyridinylmethyl)amino]-3-methylbutanamide C22H31N3O5S 详情 详情
Extended Information