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 -Drug Synthesis Database

【结构式】

【分子编号】38208

【品名】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

【CA登记号】

【分子式】C₄₉H₄₂ClN₅O₇S₃

【分子量】944.55268

【元素组成】C 62.31% H 4.48% Cl 3.75% N 7.41% O 11.86% S 10.18%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(X)

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.

参考文献中间体

合成目标

【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

Extended Information