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【结 构 式】

【分子编号】27711

【品名】methyl (2S)-2-[[4-[[(tert-butoxycarbonyl)amino]methyl]-2-(1-naphthyl)benzoyl]amino]-4-methylpentanoate

【CA登记号】

【 分 子 式 】C30H36N2O5

【 分 子 量 】504.62632

【元素组成】C 71.41% H 7.19% N 5.55% O 15.85%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(X)

Suzuki coupling of methyl 2-bromo-4-nitrobenzoate (I) with 1-naphthylboronic acid (II) provided naphthyl benzoate ester (III). The nitro group of (III) was then reduced by hydrogenation over Pd/C yielding aniline (IV). Diazotization of (IV), followed by reaction with KI gave aryl iodide (V), and subsequent halogen displacement by KCN in the presence of palladium catalyst afforded nitrile (VI). After basic hydrolysis of the methyl ester of (VI), the resulting carboxylic acid (VII) was coupled to L-leucine methyl ester (VIII) using EDC and HOBt to yield amide (IX). Reduction of the nitrile group of (IX) with NaBH4 and CoCl2 gave the corresponding amine, which was isolated as the tert-butyl carbamate (X) upon treatment with Boc2O.

1 Vasudevan, A.; et al.; Potent, highly selective, and non-thiol inhibitors of protein geranylgeranyltransferase-I. J Med Chem 1999, 42, 8, 1333.
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) 27702 methyl 2-bromo-4-nitrobenzoate C8H6BrNO4 详情 详情
(II) 27703 1-naphthylboronic acid 13922-41-3 C10H9BO2 详情 详情
(III) 27704 methyl 2-(1-naphthyl)-4-nitrobenzoate C18H13NO4 详情 详情
(IV) 27705 methyl 4-amino-2-(1-naphthyl)benzoate C18H15NO2 详情 详情
(V) 27706 methyl 4-iodo-2-(1-naphthyl)benzoate C18H13IO2 详情 详情
(VI) 27707 methyl 4-cyano-2-(1-naphthyl)benzoate C19H13NO2 详情 详情
(VII) 27708 4-cyano-2-(1-naphthyl)benzoic acid C18H11NO2 详情 详情
(VIII) 27709 methyl (2S)-2-amino-4-methylpentanoate C7H15NO2 详情 详情
(IX) 27710 methyl (2S)-2-[[4-cyano-2-(1-naphthyl)benzoyl]amino]-4-methylpentanoate C25H24N2O3 详情 详情
(X) 27711 methyl (2S)-2-[[4-[[(tert-butoxycarbonyl)amino]methyl]-2-(1-naphthyl)benzoyl]amino]-4-methylpentanoate C30H36N2O5 详情 详情

合成路线2

该中间体在本合成路线中的序号:(X)

Further acidic treatment of compund (X) regenerated the amine, which was condensed with the imidazole aldehyde (XI) in the presence of titanium isopropoxide as the water scavenger to give imine (XII). This was reduced to amine (XIII) using NaBH3CN. Finally, the title compound was obtained after acid cleavage of the trityl group of (XXXIII), followed by hydrolysis of the resulting ester (XIV).

1 Vasudevan, A.; et al.; Potent, highly selective, and non-thiol inhibitors of protein geranylgeranyltransferase-I. J Med Chem 1999, 42, 8, 1333.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(X) 27711 methyl (2S)-2-[[4-[[(tert-butoxycarbonyl)amino]methyl]-2-(1-naphthyl)benzoyl]amino]-4-methylpentanoate C30H36N2O5 详情 详情
(XI) 27712 1-trityl-1H-imidazole-4-carbaldehyde;1-Tritylimidazole-4-carboxaldehyde 33016-47-6 C23H18N2O 详情 详情
(XII) 27713 methyl (2S)-4-methyl-2-[[2-(1-naphthyl)-4-([[(E)-(1-trityl-1H-imidazol-4-yl)methylidene]amino]methyl)benzoyl]amino]pentanoate C48H44N4O3 详情 详情
(XIII) 27714 methyl (2S)-4-methyl-2-[[2-(1-naphthyl)-4-([[(1-trityl-1H-imidazol-4-yl)methyl]amino]methyl)benzoyl]amino]pentanoate C48H46N4O3 详情 详情
(XIV) 27715 methyl (2S)-2-[[4-[[(1H-imidazol-4-ylmethyl)amino]methyl]-2-(1-naphthyl)benzoyl]amino]-4-methylpentanoate C29H32N4O3 详情 详情
Extended Information