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【结 构 式】 
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【分子编号】29850 【品名】4-nitrobenzyl (3S)-3-sulfanyl-1-pyrrolidinecarboxylate 【CA登记号】 |
【 分 子 式 】C12H14N2O4S 【 分 子 量 】282.32024 【元素组成】C 51.05% H 5% N 9.92% O 22.67% S 11.36% |
合成路线1
该中间体在本合成路线中的序号：(VII)The reaction of 4-acetoxy-3-[(1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one (I) with benzyl-3-pyrrolidinocrotonate (II) gives the enimine ester (III), which is hydrolyzed with HCl to the corresponding ketoester (IV). The cyclization of (IV), through the diazo compound (V) by means of rhodium acetate, yields the bicyclic ketoester (VI). The condensation of (VI) with 1-(4-nitrobenzyloxycarbonyl)-3-mercaptopyrrolidine (VII) affords the protected carbapenem compound (VIII), which is deprotected by hydrogenation with H2 over Pd/C in THF giving 6-(1-hydroxyethyl)-2-(pyrrolidin-3-ylthio)-1-carbapen-2-em-2-carboxylic acid (IX). Finally, this compound is condensed with ethyl acetimidate (X) in a phosphate buffer.
| 【1】 Tanaka, T.; Sugimura, Y.; Miyadera, T.; Hashimoto, T.; Iino, K.; Shibata, T.; Sugawara, S.; Synthesis and in vitro activity of a new carbapenem, RS-533. J Antibiot 1983, 36, 8, 1034. |
| 【2】 Serradell, M.N.; Castaner, J.; RS-533. Drugs Fut 1985, 10, 12, 989. |
| 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) | 11687 | (2R,3R)-3-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-4-oxoazetanyl acetate | C13H25NO4Si | 详情 | 详情 | |
| (II) | 29845 | benzyl (Z)-3-(1-pyrrolidinyl)-2-butenoate | C15H19NO2 | 详情 | 详情 | |
| (III) | 29846 | benzyl (Z)-4-[(2R,3S)-3-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-4-oxoazetidinyl]-3-(1-pyrrolidinyl)-2-butenoate | C26H40N2O4Si | 详情 | 详情 | |
| (IV) | 29847 | benzyl 4-[(2R,3S)-3-[(1R)-1-hydroxyethyl]-4-oxoazetidinyl]-3-oxobutanoate | C16H19NO5 | 详情 | 详情 | |
| (V) | 29848 | 2-Diazo-4-[3(S)-(1(R)-hydroxyethyl)-4-oxoazetidin-2(R)-yl]-3-oxobutyric acid benzyl ester | C16H17N3O5 | 详情 | 详情 | |
| (VI) | 29849 | benzyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate | C16H17NO5 | 详情 | 详情 | |
| (VII) | 29850 | 4-nitrobenzyl (3S)-3-sulfanyl-1-pyrrolidinecarboxylate | C12H14N2O4S | 详情 | 详情 | |
| (VIII) | 29851 | benzyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[[(3S)-1-(4-nitrobenzyl)pyrrolidinyl]sulfanyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | C27H29N3O6S | 详情 | 详情 | |
| (IX) | 29852 | (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(3S)pyrrolidinylsulfanyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid | C13H18N2O4S | 详情 | 详情 | |
| (X) | 12831 | ethyl ethanimidoate | 1000-84-6 | C4H9NO | 详情 | 详情 |