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【结 构 式】

【分子编号】51226

【品名】methyl 8-[(tert-butoxycarbonyl)amino]octanoate

【CA登记号】

【 分 子 式 】C14H27NO4

【 分 子 量 】273.37272

【元素组成】C 61.51% H 9.96% N 5.12% O 23.41%

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:(VI)

Full protection of 8-aminooctanoic acid (I) with TMSCl in refluxing CH2Cl2 yields derivative (II), which is then coupled to acetylsalicyloyl chloride (III) by means of Et3N to provide compound (IV). Finally, the desired product is obtained by saponification of (IV) with NaOH. Alternatively, another route can be followed for the synthesis of the target compound: Curtius rearrangement of nonanedioic acid monomethyl ester (V) with DPPA and Et3N in toluene, followed by treatment with tert-BuOH, affords Boc-amino ester (VI), whose Boc group is then removed by means of HCl in dioxane to yield deprotected ester (VII). Coupling of (VII) with acetylsalicyloyl chloride (III) by means of Et3N in THF/DMF gives compound (VIII), which is finally saponified with NaOH.

1 Baughman, R.A.; Salo-Kostmayer, S.; O'Toole, D.; Rosado-Gray, C.; Tai, M.; Mercogliano, F.; Leone-Bay, A.; Freeman, J.; Studies directed at the use of a parallel synthesis matrix to increase throughput in an in vivo assay. J Med Chem 2000, 43, 19, 3573.
2 Leone-Bay, A.; Paton, D.R.; Freeman, J.; et al.; Synthesis and evaluation of compounds that facilitate the gastrointestinal absorption of heparin. J Med Chem 1998, 41, 7, 1163.
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) 47828 8-aminooctanoic acid 1002-57-9 C8H17NO2 详情 详情
(II) 47829 trimethylsilyl 8-[(trimethylsilyl)amino]octanoate C14H33NO2Si2 详情 详情
(III) 16900 2-(chlorocarbonyl)phenyl acetate; Acetylsalicyloyl chloride 5538-51-2 C9H7ClO3 详情 详情
(IV) 51224 trimethylsilyl 8-[[2-(acetoxy)benzoyl]amino]octanoate C20H31NO5Si 详情 详情
(V) 51225 9-methoxy-9-oxononanoic acid C10H18O4 详情 详情
(VI) 51226 methyl 8-[(tert-butoxycarbonyl)amino]octanoate C14H27NO4 详情 详情
(VII) 51227 8-methoxy-8-oxo-1-octanaminium chloride C9H20ClNO2 详情 详情
(VIII) 51228 methyl 8-[[2-(acetoxy)benzoyl]amino]octanoate C18H25NO5 详情 详情
Extended Information