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【结 构 式】 
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【分子编号】18246 【品名】4-nitrobenzyl 1-cyclopropyl-6-fluoro-7-[4-[((2S,4S)-4-[((4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-2-[[(4-nitrobenzyl)oxy]carbonyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl)sulfanyl]-1-[[(4-nitrobenzyl)oxy]carbonyl]pyrrolidinyl)carbonyl]-1-piperazinyl]-4-oxo-1,4-dihydro-3-quinolinecarboxylate 【CA登记号】 |
【 分 子 式 】C54H51FN8O16S 【 分 子 量 】1119.1076632 【元素组成】C 57.96% H 4.59% F 1.7% N 10.01% O 22.87% S 2.87% |
合成路线1
该中间体在本合成路线中的序号：(VI)Coupling of thioacetylproline derivative (I) with p-nitrobenzyl ester of ciprofloxacin (II) in the presence of dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) provided amide (III). Treatment with pyrrolidine in acetonitrile gave thiol (IV), which was subsequently alkylated with the carbapenem phosphate (V) in the presence of diisopropylethylamine to give thioether (VI). Then, hydrogenolytical removal of p-nitrobenzyl protecting groups in the presence of Pd-C, followed by treatment with sodium 2-ethylhexanoate in acetone provided the target disodium salt.
| 【1】 Hershberger, P.M.; Switzer, A.G.; Yelm, K.E.; Coleman, M.C.; Devries, C.A.; Rourke, F.J.; Davis, B.W.; Kraft, W.G.; Twinem, T.L.; Koenigs, P.M.; Paule, S.M.; Siehnel, R.J.; Zoutendam, P.H.; Imbus, R.; Demuth, T.P. Jr.; Preparation and antimicrobial assessment of 2-thioether-linked quinolonyl-carbapenems. J Antibiot 1998, 51, 9, 857-871. |
| 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) | 18241 | (2S,4S)-4-(acetylsulfanyl)-1-[[(4-nitrobenzyl)oxy]carbonyl]-2-pyrrolidinecarboxylic acid | C15H16N2O7S | 详情 | 详情 | |
| (II) | 18242 | 4-nitrobenzyl 1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro-3-quinolinecarboxylate | C24H23FN4O5 | 详情 | 详情 | |
| (III) | 18243 | 4-nitrobenzyl 7-[4-[((2S,4S)-4-(acetylsulfanyl)-1-[[(4-nitrobenzyl)oxy]carbonyl]pyrrolidinyl)carbonyl]-1-piperazinyl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate | C39H37FN6O11S | 详情 | 详情 | |
| (IV) | 18244 | 4-nitrobenzyl 1-cyclopropyl-6-fluoro-7-[4-[((2S,4S)-1-[[(4-nitrobenzyl)oxy]carbonyl]-4-sulfanylpyrrolidinyl)carbonyl]-1-piperazinyl]-4-oxo-1,4-dihydro-3-quinolinecarboxylate | C37H35FN6O10S | 详情 | 详情 | |
| (V) | 13224 | 4-nitrobenzyl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | 90776-59-3 | C29H27N2O10P | 详情 | 详情 |
| (VI) | 18246 | 4-nitrobenzyl 1-cyclopropyl-6-fluoro-7-[4-[((2S,4S)-4-[((4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-2-[[(4-nitrobenzyl)oxy]carbonyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl)sulfanyl]-1-[[(4-nitrobenzyl)oxy]carbonyl]pyrrolidinyl)carbonyl]-1-piperazinyl]-4-oxo-1,4-dihydro-3-quinolinecarboxylate | C54H51FN8O16S | 详情 | 详情 |