【结 构 式】 |
【分子编号】49990 【品名】2,3,5,6-Tetrachloroaniline 【CA登记号】3481-20-7 |
【 分 子 式 】C6H3Cl4N 【 分 子 量 】230.90736 【元素组成】C 31.21% H 1.31% Cl 61.41% N 6.07% |
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:(X)Acylation of tetrachloroaniline (X) with methyl oxalyl chloride (XI) provided the oxamate ester (XII), which was further hydrolyzed to the N-(tetrachlorophenyl)oxamic acid (XIII) by using LiOH. Coupling of acid (XIII) with the intermediate amine (IX) in the presence of HATU furnished the oxalic diamide (XIV). The alcohol function of (XIV) was then reoxidized to ketone (XV) employing the Dess-Martin periodinane reagent. Finally, the tert-butyl ester group of (XV) was cleaved by treatment with trifluoroacetic acid.
【1】 Ternansky, R.J.; et al.; Structure-activity relationship of a series of oxamyl dipeptide caspase inhibitors developed for the treatment of stroke. 221st ACS Natl Meet (April 1 2001, San Diego) 2001, Abst MEDI 75. |
【2】 Karanewsky, D.S.; Ternansky, R.J. (Idun Pharmaceuticals, Inc.); C-Terminal modified oxamyl dipeptides as inhibitors of the ICE/ced-3 family of cysteine proteases. EP 1091930; WO 0001666 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(IX) | 49989 | tert-butyl (3S)-3-[[(2S)-2-amino-3-methylbutanoyl]amino]-4-hydroxy-5-(2,3,5,6-tetrafluorophenoxy)pentanoate | C20H28F4N2O5 | 详情 | 详情 | |
(X) | 49990 | 2,3,5,6-Tetrachloroaniline | 3481-20-7 | C6H3Cl4N | 详情 | 详情 |
(XI) | 26971 | 2-methoxy-2-oxoacetyl chloride | 5781-53-3 | C3H3ClO3 | 详情 | 详情 |
(XII) | 49991 | methyl 2-oxo-2-(2,3,5,6-tetrachloroanilino)acetate | C9H5Cl4NO3 | 详情 | 详情 | |
(XIII) | 49992 | 2-oxo-2-(2,3,5,6-tetrachloroanilino)acetic acid | C8H3Cl4NO3 | 详情 | 详情 | |
(XIV) | 49993 | tert-butyl (3S)-4-hydroxy-3-[((2S)-3-methyl-2-[[2-oxo-2-(2,3,5,6-tetrachloroanilino)acetyl]amino]butanoyl)amino]-5-(2,3,5,6-tetrafluorophenoxy)pentanoate | C28H29Cl4F4N3O7 | 详情 | 详情 | |
(XV) | 49994 | tert-butyl (3S)-3-[((2S)-3-methyl-2-[[2-oxo-2-(2,3,5,6-tetrachloroanilino)acetyl]amino]butanoyl)amino]-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoate | C28H27Cl4F4N3O7 | 详情 | 详情 |
Extended Information