• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】38756

【品名】tert-butyl (2S,4R)-2-[(tert-butylamino)carbonyl]-4-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-1-piperidinecarboxylate

【CA登记号】

【 分 子 式 】C18H34N2O4S

【 分 子 量 】374.54504

【元素组成】C 57.72% H 9.15% N 7.48% O 17.09% S 8.56%

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:(II)

The reaction of (2S,4R)-1-(tert-butoxycarbonyl)-N-tert-butyl-4-hydroxypiperidine-2-carboxamide (I) with MsCl and TEA gives the mesylate (II), which is treated with tetrabutylammonium bromide in refluxing THF to yield the corresponding 4-bromo derivative (III). The reaction of (III) with potassium thioacetate, followed by hydrolysis with NaOH affords the sodium thiolate (IV), which is condensed with 4-chloropyridine (V) to provide (2S,4R)-1-(tert-butoxycarbonyl)-N-tert-butyl-4-(4-pyridylsulfanyl)piperidine-2-carboxamide (VI). The deprotection of (VI) with TFA or HCl in dioxane gives intermediate (VII), which is condensed with epoxide (VIII) in refluxing ethanol to obtain the expected addition compound (IX). The deprotection of (IX) with TFA or HCl as before yields the amide (X), which is finally condensed with 2-(2,6-dimethylphenoxy)acetic acid (XI) by means of BOP and DIEA to furnish the target diamide.

1 Anderson, P.C.; Beaulieu, P.L.; Cameron, D.R.; et al.; 2'6'-Dimethylphenoxyacetyl: A new achiral high affinity P3-P2 ligand for peptidomimetic-based HIV protease inhibitors. J Med Chem 2000, 43, 6, 1094.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 19736 tert-butyl (2S,4R)-2-[(tert-butylamino)carbonyl]-4-hydroxy-1-piperidinecarboxylate C15H28N2O4 详情 详情
(II) 38756 tert-butyl (2S,4R)-2-[(tert-butylamino)carbonyl]-4-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-1-piperidinecarboxylate C18H34N2O4S 详情 详情
(III) 38757 tert-butyl (2S,4S)-4-bromo-2-[(tert-butylamino)carbonyl]-1-piperidinecarboxylate C15H27BrN2O3 详情 详情
(IV) 38762   C15H27N2NaO3S 详情 详情
(V) 32889 4-chloropyridine 7379-35-3 C5H4ClN 详情 详情
(VI) 38758 tert-butyl (2S,4R)-2-[(tert-butylamino)carbonyl]-4-(4-pyridinylsulfanyl)-1-piperidinecarboxylate C20H31N3O3S 详情 详情
(VII) 38759 (2S,4R)-N-(tert-butyl)-4-(4-pyridinylsulfanyl)-2-piperidinecarboxamide C15H23N3OS 详情 详情
(VIII) 19730 tert-butyl (1S)-1-[(2S)oxiranyl]-2-phenylethylcarbamate 98737-29-2 C15H21NO3 详情 详情
(IX) 38760 tert-butyl (1S,2R)-1-benzyl-3-[(2S,4R)-2-[(tert-butylamino)carbonyl]-4-(4-pyridinylsulfanyl)piperidinyl]-2-hydroxypropylcarbamate C30H44N4O4S 详情 详情
(X) 38761 (2S,4R)-1-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(tert-butyl)-4-(4-pyridinylsulfanyl)-2-piperidinecarboxamide C25H36N4O2S 详情 详情
(XI) 38270 2-(2,6-dimethylphenoxy)acetic acid C10H12O3 详情 详情
Extended Information