(8R,11S)-8-isobutyl-11-[(methylamino)carbonyl]-9-oxo-2-oxa-10-azabicyclo[11.2.2]heptadeca-1(15),13,16-triene-7-carboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】25401

【品名】(8R,11S)-8-isobutyl-11-[(methylamino)carbonyl]-9-oxo-2-oxa-10-azabicyclo[11.2.2]heptadeca-1(15),13,16-triene-7-carboxylic acid

【CA登记号】

【分子式】C₂₂H₃₂N₂O₅

【分子量】404.50656

【元素组成】C 65.32% H 7.97% N 6.93% O 19.78%

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：(XVI)

Then, cyclization of (XIV) under Mitsunobu conditions furnished macrocyclic ether (XV). The deprotection of (XV) with trifluoroacetic acid yielded carboxylic acid (XVI), which was treated with silyl protected hydroxylamine to afford hydroxamic acid (XVII). The required isomer of (XVII) was isolated using reverse-phase HPLC.

参考文献中间体

合成目标

【1】 Sheppard, G.S.; Guo, Y.; Siummers, J.B.; Holms, J.H.; Steinman, D.H.; Michaelides, M.R.; Florjancic, A.S.; Xu, L.; Davidsen, S.K. (Abbott Laboratories Inc.); Macrocyclic inhibitors of matrix metalloproteinases and TNFalpha secretion. EP 1021423; WO 9830551 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XIV)	25399	tert-butyl (3R)-3-([[(1S)-1-(4-hydroxybenzyl)-2-(methylamino)-2-oxoethyl]amino]carbonyl)-2-(4-hydroxybutyl)-5-methylhexanoate	C₂₆H₄₂N₂O₆	详情	详情
(XV)	25400	tert-butyl (8R,11S)-8-isobutyl-11-[(methylamino)carbonyl]-9-oxo-2-oxa-10-azabicyclo[11.2.2]heptadeca-1(15),13,16-triene-7-carboxylate	C₂₆H₄₀N₂O₅	详情	详情
(XVI)	25401	(8R,11S)-8-isobutyl-11-[(methylamino)carbonyl]-9-oxo-2-oxa-10-azabicyclo[11.2.2]heptadeca-1(15),13,16-triene-7-carboxylic acid	C₂₂H₃₂N₂O₅	详情	详情
(XVII)	25402	(8R,11S)-N(7)-hydroxy-8-isobutyl-N(11)-methyl-9-oxo-2-oxa-10-azabicyclo[11.2.2]heptadeca-1(15),13,16-triene-7,11-dicarboxamide	C₂₂H₃₃N₃O₅	详情	详情

Extended Information