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【结 构 式】 
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【分子编号】54646 【品名】diethyl 2-[{3-[(tert-butoxycarbonyl)amino]propyl}(2-ethoxy-3,4-dioxo-1-cyclobuten-1-yl)amino]ethylphosphonate 【CA登记号】 |
【 分 子 式 】C20H35N2O8P 【 分 子 量 】462.480342 【元素组成】C 51.94% H 7.63% N 6.06% O 27.68% P 6.7% |
合成路线1
该中间体在本合成路线中的序号：(VI)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 |