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【结 构 式】

【分子编号】49413

【品名】bis(4-methoxyphenyl) 3-bromopropylphosphonate

【CA登记号】

【 分 子 式 】C17H20BrO5P

【 分 子 量 】415.220562

【元素组成】C 49.18% H 4.85% Br 19.24% O 19.27% P 7.46%

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)

The reaction of 1,3-dibromopropane (I) with triethyl phosphite (II) at 160 C gives triethyl 3-bromopropylphosphonate (III), which is treated with Tms-Br and water to yield the corresponding phosphonic acid (IV). The reaction of (IV) with PCl3 in refluxing chloroform affords the acyl chloride (V), which is treated with 4-methoxyphenol (VI) and pyridine to provide the expected 4-methoxyphenyl diester (VII). The reaction of (VII) with N,O-bis(tert-butoxycarbonyl)hydroxylamine (VIII) by means of NaH in DMF gives the fully protected hydroxyamino derivative (IX), which by treatment with TFA in dichloromethane yields 3-(hydroxyamino)propylphosphonic acid 4-methoxyphenyl diester (X). Finally, this compound is acylated with Ac-Cl and TEA in ethyl ether to afford the target N-acetylhydroxyamino compound.

1 Reichenberg, A.; et al.; Diaryl ester prodrugs of FR900098 with improved in vivo antimalarial activity. Bioorg Med Chem Lett 2001, 11, 6, 833.
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) 12581 1,3-Dibromopropane 109-64-8 C3H6Br2 详情 详情
(II) 15487 triethyl phosphite 122-52-1 C6H15O3P 详情 详情
(III) 39080 diethyl 3-bromopropylphosphonate C7H16BrO3P 详情 详情
(IV) 39105 3-bromopropylphosphonic acid 1190-09-6 C3H8BrO3P 详情 详情
(V) 49412 3-bromopropylphosphonic dichloride C3H6BrCl2OP 详情 详情
(VI) 32744 4-methoxyphenol 150-76-5 C7H8O2 详情 详情
(VII) 49413 bis(4-methoxyphenyl) 3-bromopropylphosphonate C17H20BrO5P 详情 详情
(VIII) 34722 2-[([[(tert-butoxycarbonyl)amino]oxy]carbonyl)oxy]-2-methylpropane C10H19NO5 详情 详情
(IX) 49414 5-(tert-butoxycarbonyl)-1,1-bis(4-methoxyphenoxy)-9,9-dimethyl-1,7-dioxo-6,8-dioxa-5-aza-1lambda(5)-phosphadecane C27H38NO10P 详情 详情
(X) 49415 bis(4-methoxyphenyl) 3-(hydroxyamino)propylphosphonate C17H22NO6P 详情 详情
Extended Information