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【结 构 式】

【分子编号】43380

【品名】3-(benzyloxy)-1-[3-[3,5-di(tert-butyl)-4-hydroxyphenyl]propyl]-2-methyl-4(1H)-pyridinone

【CA登记号】

【 分 子 式 】C30H39NO3

【 分 子 量 】461.6446

【元素组成】C 78.05% H 8.52% N 3.03% O 10.4%

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:(VII)

Catalytic hydrogenation of 3,5-di-tert-butyl-4-hydroxycinnamic acid (I) afforded the saturated carboxylic acid (II), which was converted into amide (IV) via the corresponding acid chloride (III). Reduction of the amide function of (IV) by means of LiAlH4 furnished the primary amine (V). This was condensed with O-benzyl maltol (VI) to produce the pyridone (VII). After hydrogenolysis of the benzyl protecting group of (VII), the title compound was isolated as the corresponding mesylate salt.

1 Malcolm, C.S.; Bebbington, D.; Monck, N.J.T.; Palmer, A.M.; Gaur, S.; Benwell, K.; Porter, R.H.P.; Harvey, V.; 3,5-Disubstituted-4-hydroxyphenyls linked to 3-hydroxy-2-methyl-4(1H)-pyridinone: Potent inhibitors of lipid peroxidation and cell toxicity. J Med Chem 2000, 43, 15, 2779.
2 Malcolm, C.; Porter, R.; Bebbington, D.; Palmer, A.; Gaur, S.; Monck, N. (Vernalis Research Ltd.); Ortho-hydroxypyridinone derivs. as iron chelating and antioxidant agents. EP 1027335; WO 9923075 .
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) 43375 (E)-3-[3,5-di(tert-butyl)-4-hydroxyphenyl]-2-propenoic acid 22014-01-3 C17H24O3 详情 详情
(II) 43376 3-[3,5-di(tert-butyl)-4-hydroxyphenyl]propionic acid 20170-32-5 C17H26O3 详情 详情
(III) 43777 5,5,8,8-tetramethyl-N-(2-nitrophenyl)-5,6,7,8-tetrahydro-2-naphthalenamine; N-(2-nitrophenyl)-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)amine C20H24N2O2 详情 详情
(IV) 43378 3-[3,5-di(tert-butyl)-4-hydroxyphenyl]propanamide C17H27NO2 详情 详情
(V) 43379 4-(3-aminopropyl)-2,6-di(tert-butyl)phenol C17H29NO 详情 详情
(VI) 12074 3-(Benzyloxy)-2-methyl-4H-pyran-4-one;3-(benzyloxy)-2-methylpyran-4-one 61049-69-2 C13H12O3 详情 详情
(VII) 43380 3-(benzyloxy)-1-[3-[3,5-di(tert-butyl)-4-hydroxyphenyl]propyl]-2-methyl-4(1H)-pyridinone C30H39NO3 详情 详情
Extended Information