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【结 构 式】 
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【药物名称】Piperacillin 【化学名称】4-Ethyl-2,3-dioxopiperazinecarbonylampicillin 【CA登记号】61477-96-1 【 分 子 式 】C23H27N5O7S 【 分 子 量 】517.56494 |
【开发单位】 【药理作用】 |
合成路线1
The cyclization of diethyl oxalate (I) with N-ethylethylenediamine (II) in ethanol gives ethyl-2,3-dioxopiperazine (III), which by reaction first with trimethylsilyl chloride and triethytamine and then with phosgene in THF is converted into 4-ethyl-2,3-dioxopiperazine-1-carboxylic acid chloride (IV). Finally, this compound is condensed with 6-D-(-)-alpha-aminophenylacetamidopenicillanic acid (V) by means of triethylamine in THF - water.
| 【1】 Saikawa, I.; et al.; Penicillins and cephalosporins and process for producing the same. DE 2519400; FR 2269937; FR 2320295; GB 1508062 . |
| 【2】 Loren, J.G.; Castañer, J.; Piperacillin. Drugs Fut 1978, 3, 11, 829. |
| 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) | 17571 | Diethyl oxalate; Ethyl 2-ethoxy-2-oxoacetate | 95-92-1 | C6H10O4 | 详情 | 详情 |
| (II) | 39928 | N(1)-ethyl-1,2-ethanediamine; N-(2-aminoethyl)-N-ethylamine | 110-72-5 | C4H12N2 | 详情 | 详情 |
| (III) | 39929 | 1-ethyl-2,3-piperazinedione | 59702-31-7 | C6H10N2O2 | 详情 | 详情 |
| (IV) | 24305 | 4-ethyl-2,3-dioxo-1-piperazinecarbonyl chloride | 59703-00-3 | C7H9ClN2O3 | 详情 | 详情 |
| (V) | 31107 | (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylethanoyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid | 69-53-4 | C16H19N3O4S | 详情 | 详情 |