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【结 构 式】 
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【分子编号】38207 【品名】benzhydryl 7-([2-[2-[(tert-butoxycarbonyl)amino]-5-chloro-1,3-thiazol-4-yl]-2-[(trityloxy)imino]acetyl]amino)-3-([[(2,6-diamino-4-pyrimidinyl)sulfanyl]methyl]sulfanyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 【CA登记号】 |
【 分 子 式 】C54H48ClN9O7S4 【 分 子 量 】1098.74828 【元素组成】C 59.03% H 4.4% Cl 3.23% N 11.47% O 10.19% S 11.67% |
合成路线1
该中间体在本合成路线中的序号：(XIII)In a related procedure, chloromethylsulfanyl derivative (IX) was condensed with 2,4-diamino-6-mercaptopyrimidine (XI) to give thioacetal (XIII), which was then deprotected with trifluoroacetic acid-promoted cleavage of Boc, trityl and benzhydryl protecting groups of (XIII) yielded the title compound.
| 【1】 Oh, S.H.; Lee, C.-S.; Ryu, E.-J.; Paek, K.-S.; Kim, M.Y.; Youn, H.; Synthesis and antibacterial activities of novel C(3)-aminopyrimidinyl substituted cephalosporins including against respiratory tract pathogens. Bioorg Med Chem Lett 2000, 10, 18, 2123. |
| 【2】 Paek, K.S.; Ryu, E.J.; Oh, S.H.; Lee, C.S.; Lee, S.H.; Kim, M.Y.; Synthesis and antibacterial activities of LB10827, a new oral cephalosporin antibiotic. 39th Intersci Conf Antimicrob Agents Chemother (Sept 26 1999, San Francisco) 1999, Abst F397. |
| 【3】 Kim, M.Y.; Oh, S.H.; Kim, Y.Z.; Moon, K.Y.; Lee, C.S.; Ryu, E.J.; Paek, K.S.; Lee, S.H. (LG Chem Ltd.); Novel cephalosporin cpds., processes for preparation thereof and antimicrobial compsns. containing the same. WO 9958535 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IX) | 38205 | benzhydryl 7-([2-[2-[(tert-butoxycarbonyl)amino]-5-chloro-1,3-thiazol-4-yl]-2-[(trityloxy)imino]acetyl]amino)-3-[(chloromethyl)sulfanyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C50H43Cl2N5O7S3 | 详情 | 详情 | |
| (XI) | 38206 | 2,6-diamino-4-pyrimidinethiol; 2,6-diamino-4-pyrimidinylhydrosulfide | 81012-96-6 | C4H6N4S | 详情 | 详情 |
| (XIII) | 38207 | benzhydryl 7-([2-[2-[(tert-butoxycarbonyl)amino]-5-chloro-1,3-thiazol-4-yl]-2-[(trityloxy)imino]acetyl]amino)-3-([[(2,6-diamino-4-pyrimidinyl)sulfanyl]methyl]sulfanyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C54H48ClN9O7S4 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XIII)Thioacetate ester (VIII) was hydrolyzed to thiol (X) by treatment with morpholine and triethylamine. The iodomethylsulfanyl pyrimidine (XII) was prepared by alkylation of 2,4-diamino-6-mercaptopyrimidine (XI) with bromochloromethane, followed by displacement of the chlorine with NaI in acetone. Alkylation of thiol (X) with iodide (XII) gave rise to thioacetal (XIII). Finally, trifluoroacetic acid-promoted cleavage of Boc, trityl and benzhydryl protecting groups of (XIII) yielded the title compound.
| 【1】 Oh, S.H.; Lee, C.-S.; Ryu, E.-J.; Paek, K.-S.; Kim, M.Y.; Youn, H.; Synthesis and antibacterial activities of novel C(3)-aminopyrimidinyl substituted cephalosporins including against respiratory tract pathogens. Bioorg Med Chem Lett 2000, 10, 18, 2123. |
| 【2】 Kim, M.Y.; Oh, S.H.; Kim, Y.Z.; Moon, K.Y.; Lee, C.S.; Ryu, E.J.; Paek, K.S.; Lee, S.H. (LG Chem Ltd.); Novel cephalosporin cpds., processes for preparation thereof and antimicrobial compsns. containing the same. WO 9958535 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIII) | 38204 | benzhydryl 3-(acetylsulfanyl)-7-([2-[2-[(tert-butoxycarbonyl)amino]-5-chloro-1,3-thiazol-4-yl]-2-[(trityloxy)imino]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C51H44ClN5O8S3 | 详情 | 详情 | |
| (X) | 38208 | benzhydryl 7-([2-[2-[(tert-butoxycarbonyl)amino]-5-chloro-1,3-thiazol-4-yl]-2-[(trityloxy)imino]acetyl]amino)-8-oxo-3-sulfanyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C49H42ClN5O7S3 | 详情 | 详情 | |
| (XI) | 38206 | 2,6-diamino-4-pyrimidinethiol; 2,6-diamino-4-pyrimidinylhydrosulfide | 81012-96-6 | C4H6N4S | 详情 | 详情 |
| (XII) | 38209 | 2-amino-6-[(iodomethyl)sulfanyl]-4-pyrimidinylamine; 6-[(iodomethyl)sulfanyl]-2,4-pyrimidinediamine | C5H7IN4S | 详情 | 详情 | |
| (XIII) | 38207 | benzhydryl 7-([2-[2-[(tert-butoxycarbonyl)amino]-5-chloro-1,3-thiazol-4-yl]-2-[(trityloxy)imino]acetyl]amino)-3-([[(2,6-diamino-4-pyrimidinyl)sulfanyl]methyl]sulfanyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C54H48ClN9O7S4 | 详情 | 详情 |