benzhydryl (6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】61475

【品名】benzhydryl (6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

【CA登记号】

【分子式】C₂₁H₂₀N₂O₃S

【分子量】380.46748

【元素组成】C 66.3% H 5.3% N 7.36% O 12.62% S 8.43%

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：(I)

Coupling of the amino cephem derivative (I) with oximino acid (II) by means of POCl3/pyridine produces amide (III). Subsequent condensation of (III) with bis(dimethylamino)t-butoxymethane affords enamine (IV), which is further hydrolyzed to aldehyde (V) under acidic conditions. Treatment of aldehyde (V) with trifluoromethanesulfonic anhydride and pyridine produces the vinyl triflate (VI)

参考文献中间体

合成目标

【1】 Lee, C.; Kim, G.; Jang, Y.; Koo, K.; Cho, Y.; Youn, H.; Synthesis and antibacterial activities of LB11058, a novel anti-MRSA cephalosporin antibiotic. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-329.
【2】 Lee, S.-H.; Lee, C.-S.; Ryu, E.-J.; Jang, Y.-J.; Kim, G.-T.; Cho, Y.-r.; Joo, H.-Y.; Shin, J.-E.; Koo, K.-D. (LG Chem Ltd.); Novel cephalosporin cpds. and process for preparing the same. WO 0372582 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	61475	benzhydryl (6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	C₂₁H₂₀N₂O₃S	详情	详情
(II)	38203	2-[2-[(tert-butoxycarbonyl)amino]-5-chloro-1,3-thiazol-4-yl]-2-[(trityloxy)imino]acetic acid	C₂₉H₂₆ClN₃O₅S	详情	详情
(III)	61476	benzhydryl (6R,7R)-7-({2-{2-[(tert-butoxycarbonyl)amino]-5-chloro-1,3-thiazol-4-yl}-2-[(trityloxy)imino]acetyl}amino)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	C₅₀H₄₄ClN₅O₇S₂	详情	详情
(IV)	61477	benzhydryl (6R,7R)-7-({2-{2-[(tert-butoxycarbonyl)amino]-5-chloro-1,3-thiazol-4-yl}-2-[(trityloxy)imino]acetyl}amino)-3-[(E)-2-(dimethylamino)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	C₅₃H₄₉ClN₆O₇S₂	详情	详情
(V)	61478	benzhydryl (6R,7R)-7-({2-{2-[(tert-butoxycarbonyl)amino]-5-chloro-1,3-thiazol-4-yl}-2-[(trityloxy)imino]acetyl}amino)-8-oxo-3-(3-oxopropyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	C₅₂H₄₆ClN₅O₈S₂	详情	详情
(VI)	61479	benzhydryl (6R,7R)-7-({2-{2-[(tert-butoxycarbonyl)amino]-5-chloro-1,3-thiazol-4-yl}-2-[(trityloxy)imino]acetyl}amino)-8-oxo-3-((E)-2-{[(trifluoromethyl)sulfonyl]oxy}ethenyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	C₅₂H₄₃ClF₃N₅O₁₀S₃	详情	详情

Extended Information