methyl 2-oxo-2-(2,3,5,6-tetrachloroanilino)acetate -Drug Synthesis Database

【结构式】

【分子编号】49991

【品名】methyl 2-oxo-2-(2,3,5,6-tetrachloroanilino)acetate

【CA登记号】

【分子式】C₉H₅Cl₄NO₃

【分子量】316.95444

【元素组成】C 34.11% H 1.59% Cl 44.74% N 4.42% O 15.14%

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：(XII)

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.

参考文献中间体

合成目标

【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