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【结 构 式】

【分子编号】54644

【品名】diethyl vinylphosphonate

【CA登记号】

【 分 子 式 】C6H13O3P

【 分 子 量 】164.141182

【元素组成】C 43.9% H 7.98% O 29.24% P 18.87%

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:(III)

The monoprotection of propane-1,3-diamine (I) with Boc2O in dichloromethane gives the N-(3-aminopropyl)carbamic acid tert-butyl ester (II), which is condensed with vinylphosphonic acid diethyl ester (III) to yield the aminoethylphosphonic ester derivative (IV). The condensation of (IV) with 3,4-diethoxycyclobutene-1,2-dione (V) in ethanol affords the disubstituted 2-aminoethylphosphonic ester derivative (VI), which is cyclized by means of trifluoroacetic acid in dichloromethane to provide the bicyclic phosphonic ester (VII). Finally, the phosphonic ester group of (VII) is hydrolyzed by means of trimethylsilyl bromide in dichloromethane to furnish the target phosphonic acid.

1 Kinney, W.A.; Schmid, J.; Asselin, A.A. (Wyeth); Process for the preparation of [2-((8.9)-dioxo-2,6-diazabicyclo[5.2.0]-non-1(7)-en-2-yl)ethyl]phosphonic acid. US 5990307 .
2 Kinney, W.A.; Schmid, J.; Asselin, A.A. (Wyeth); Process for the preparation of [2-((8,9)-dioxo-2,6-diazabicyclo[5.2.0]-non-1(7)-en-2-yl)-ethyl]phosphonic acid. WO 9906417 .
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) 19331 3-aminopropylamine; 1,3-propanediamine 109-76-2 C3H10N2 详情 详情
(II) 52474 1,1-dimethylethyl 3-aminopropylcarbamate C8H18N2O2 详情 详情
(III) 54644 diethyl vinylphosphonate C6H13O3P 详情 详情
(IV) 54645 diethyl 2-({3-[(tert-butoxycarbonyl)amino]propyl}amino)ethylphosphonate C14H31N2O5P 详情 详情
(V) 30975 3,4-diethoxy-3-cyclobutene-1,2-dione 5231-87-8 C8H10O4 详情 详情
(VI) 54646 diethyl 2-[{3-[(tert-butoxycarbonyl)amino]propyl}(2-ethoxy-3,4-dioxo-1-cyclobuten-1-yl)amino]ethylphosphonate C20H35N2O8P 详情 详情
(VII) 54142 diethyl 2-[8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl]ethylphosphonate n/a C13H21N2O5P 详情 详情
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