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【结 构 式】

【分子编号】53177

【品名】(2R,3S)-6-[({[(5S)-5-amino-6-methoxy-6-oxohexyl]amino}carbonyl)oxy]-3-(tert-butoxycarbonyl)-2-(4-hydroxybenzyl)hexanoic acid

【CA登记号】n/a

【 分 子 式 】C26H40N2O9

【 分 子 量 】524.61168

【元素组成】C 59.53% H 7.69% N 5.34% O 27.45%

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:(XVII)

Condensation of carbonate (XIV) with N-alpha-Cbz-lysine methyl ester (XV) afforded the carbamate (XVI). The benzyl ester and N-Cbz protecting groups of (XVI) were then removed by catalytic hydrogenolysis, yielding amino acid (XVII), which was subjected to intramolecular cyclization in the presence of BOP to furnish the macrocyclic compound (XVIII). After conversion of the phenolic hydroxyl of (XVIII) to the aryl triflate (XIX), Suzuki coupling with 2-(trifluoromethyl)phenylboronic acid (XX) provided the biphenyl derivative (XXI).

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
(XIV) 53175 1-benzyl 4-(tert-butyl) (2R,3S)-2-[4-(benzyloxy)benzyl]-3-(3-{[(4-nitrophenoxy)carbonyl]oxy}propyl)butanedioate n/a C39H41NO10 详情 详情
(XV) 35087 methyl (2S)-6-amino-2-[[(benzyloxy)carbonyl]amino]hexanoate C15H22N2O4 详情 详情
(XVI) 53176 17-benzyl 16-(tert-butyl) 5-methyl (5S,16S,17R)-18-[4-(benzyloxy)phenyl]-3,11-dioxo-1-phenyl-2,12-dioxa-4,10-diazaoctadecane-5,16,17-tricarboxylate n/a C48H58N2O11 详情 详情
(XVII) 53177 (2R,3S)-6-[({[(5S)-5-amino-6-methoxy-6-oxohexyl]amino}carbonyl)oxy]-3-(tert-butoxycarbonyl)-2-(4-hydroxybenzyl)hexanoic acid n/a C26H40N2O9 详情 详情
(XVIII) 53178 12-(tert-butyl) 8-methyl (8S,11R,12S)-11-(4-hydroxybenzyl)-2,10-dioxo-1-oxa-3,9-diazacyclopentadecane-8,12-dicarboxylate n/a C26H38N2O8 详情 详情
(XIX) 53179 12-(tert-butyl) 8-methyl (8S,11R,12S)-2,10-dioxo-11-(4-{[(trifluoromethyl)sulfonyl]amino}benzyl)-1-oxa-3,9-diazacyclopentadecane-8,12-dicarboxylate n/a C27H38F3N3O9S 详情 详情
(XX) 53180 2-Trifluoromethylbenzeneboronic acid; 2-Trifluoromethylphenylboronic acid; o-Trifluoromethylphenylboronic acid 1423-27-4 C7H6BF3O2 详情 详情
(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
Extended Information