(8S,11R,12S)-8-({[2-(4-morpholinyl)-2-oxoethyl]amino}carbonyl)-2,10-dioxo-11-{[2'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methyl}-1-oxa-3,9-diazacyclopentadecane-12-carboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】53184

【品名】(8S,11R,12S)-8-({[2-(4-morpholinyl)-2-oxoethyl]amino}carbonyl)-2,10-dioxo-11-{[2'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methyl}-1-oxa-3,9-diazacyclopentadecane-12-carboxylic acid

【CA登记号】n/a

【分子式】C₃₄H₄₁F₃N₄O₈

【分子量】690.7169096

【元素组成】C 59.12% H 5.98% F 8.25% N 8.11% O 18.53%

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：(XXV)

Saponification of the methyl ester (XXI) using LiOH gave the carboxylic acid (XXII). This was coupled with the glycine amide (XXIII) to produce adduct (XXIV). The desired hydroxamic acid was then obtained by trifluoroacetic acid-promoted cleavage of the tert-butyl ester of (XXIV), followed by coupling of the resulting carboxylic acid (XXV) with hydroxylamine.

参考文献中间体

合成目标

【1】 Xue, C.-B.; et al.; Discovery of macrocyclic hydroxamic acids containing biphenylmethyl derivatives at P1', a series of selective TNF-alpha converting enzyme inhibitors with potent cellular activity in the inhibition of TNF-alpha release. J Med Chem 2001, 44, 21, 3351.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XXI)	53181	12-(tert-butyl) 8-methyl (8S,11R,12S)-2,10-dioxo-11-{[2'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methyl}-1-oxa-3,9-diazacyclopentadecane-8,12-dicarboxylate	n/a	C₃₃H₄₁F₃N₂O₇	详情	详情
(XXII)	53182	(8S,11R,12S)-12-(tert-butoxycarbonyl)-2,10-dioxo-11-{[2'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methyl}-1-oxa-3,9-diazacyclopentadecane-8-carboxylic acid	n/a	C₃₂H₃₉F₃N₂O₇	详情	详情
(XXIII)	35094	2-amino-1-(4-morpholinyl)-1-ethanone		C₆H₁₂N₂O₂	详情	详情
(XXIV)	53183	tert-butyl (8S,11R,12S)-8-({[2-(4-morpholinyl)-2-oxoethyl]amino}carbonyl)-2,10-dioxo-11-{[2'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methyl}-1-oxa-3,9-diazacyclopentadecane-12-carboxylate	n/a	C₃₈H₄₉F₃N₄O₈	详情	详情
(XXV)	53184	(8S,11R,12S)-8-({[2-(4-morpholinyl)-2-oxoethyl]amino}carbonyl)-2,10-dioxo-11-{[2'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methyl}-1-oxa-3,9-diazacyclopentadecane-12-carboxylic acid	n/a	C₃₄H₄₁F₃N₄O₈	详情	详情

Extended Information