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【结 构 式】 
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【分子编号】24309 【品名】phenethyl (2S,6R)-6-(formylamino)-3,3-dimethyl-7-oxo-6-[[(3,3,3-trichloropropanoyl)oxy]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 【CA登记号】 |
【 分 子 式 】C20H22Cl3N3O6S 【 分 子 量 】538.8354 【元素组成】C 44.58% H 4.12% Cl 19.74% N 7.8% O 17.82% S 5.95% |
合成路线1
该中间体在本合成路线中的序号：(VI)The acylation of 3,4-dihydroxyphenylglycine (I) with 4-ethyl-2,3-dioxopiperazin-1-ylcarbonyl chloride (II) by means of N,N-diethyl-1,1,1-trimethylsilylamine (DTSA) gives the corresponding N-acyl derivative (III), which is acetylated with acetic anhydride and pyridine in THF yielding the corresponding diacetoxy compound (IV). The condensation of (IV) with benzyl 6B-amino-6a-formamidopenicillanate (V) [obtained from the trichloroethoxycarbonyl derivative (VI)] by means of dicyclohexyl carbodiimide (DCC) in dichloroethane affords the fully protected compound (VII), which is debenzylated by hydrogenolysis with H2 over Pd/C in THF - water giving the free acid (VIII). Finally, this compound is desacetylated with Subtilisin Calsberg.
| 【1】 Milner, P.H. (SmithKline Beecham plc); beta -Lactam antibacterial agents. EP 0071395; GB 2107307; US 4539149; US 4609652; US 4877783 . |
| 【2】 Prous, J.; Castaner, J.; Formidacillin sodium. Drugs Fut 1986, 11, 9, 739. |
| 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) | 24304 | 2-amino-2-(3,4-dihydroxyphenyl)acetic acid | 56144-53-7 | C8H9NO4 | 详情 | 详情 |
| (II) | 24305 | 4-ethyl-2,3-dioxo-1-piperazinecarbonyl chloride | 59703-00-3 | C7H9ClN2O3 | 详情 | 详情 |
| (III) | 24306 | 2-(3,4-dihydroxyphenyl)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]acetic acid | C15H17N3O7 | 详情 | 详情 | |
| (IV) | 24307 | 2-[Bis(methoxycarbonyl)phenyl]-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarboxamido)acetic acid | C17H19N3O8 | 详情 | 详情 | |
| (V) | 24308 | phenethyl (2S,6S)-6-amino-6-(formylamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | C17H21N3O4S | 详情 | 详情 | |
| (VI) | 24309 | phenethyl (2S,6R)-6-(formylamino)-3,3-dimethyl-7-oxo-6-[[(3,3,3-trichloropropanoyl)oxy]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | C20H22Cl3N3O6S | 详情 | 详情 | |
| (VII) | 24310 | 6(S)-[2-[3,4-Bis(methoxycarbonyl)phenyl]-2-(4-ethyl-2,3-ddioxopiperazin-1-ylcarboxamido)acetamido]-6-(formamido)-2,2-dimethylpenam-3(S)-carboxylic acid benzyl ester; 6(S)-[2-[3,4-Bis(methoxycarbonyl)phenyl]-2-(4-ethyl-2,3-ddioxopiperazin-1-ylcarboxamido)acetamido]-6-(formamido)-2,2-dimethylpenam-3(S)-carboxylic acid benzyl ester | C34H38N6O11S | 详情 | 详情 | |
| (VIII) | 24311 | 6(S)-[2-[3,4-Bis(methoxycarbonyl)phenyl]-2-(4-ethyl-2,3-ddioxopiperazin-1-ylcarboxamido)acetamido]-6-(formamido)-2,2-dimethylpenam-3(S)-carboxylic acid; 6(S)-[2-[3,4-Bis(methoxycarbonyl)phenyl]-2-(4-ethyl-2,3-ddioxopiperazin-1-ylcarboxamido)acetamido]-6-(formamido)-2,2-dimethylpenam-3(S)-carboxylic acid | C26H30N6O11S | 详情 | 详情 |