benzhydryl 7-[([(7R)-7-amino-2-[(benzhydryloxy)carbonyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl)sulfanyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】23010

【品名】benzhydryl 7-[([(7R)-7-amino-2-[(benzhydryloxy)carbonyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl)sulfanyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate

【CA登记号】

【分子式】C₄₁H₃₄N₆O₅S₂

【分子量】754.8904

【元素组成】C 65.23% H 4.54% N 11.13% O 10.6% S 8.5%

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)

2-[1(S)-(3,4-dihydroxyphenyl)-1-(diphenylmethoxycarbonyl)methoxyimino]-2-[2-(triphenylmethylamino)thiazol-4-yl]-acetic acid (IX) is condensed with 7beta-amino-3-[2-(diphenylmethoxycarbonyl)-5-methyl-s-triazolo[1,5-a]pyrimidin-7-ylthiomethyl]-3-cephem-4-carboxylic acid diphenylmethyl ester (X) by means of dicyclohexylcarbodiimide (DCC) in dichloromethane giving the protected final product (XI). Finally, this compound is deprotected by treatment first with trifluoroacetic acid and then with NaHCO3 in water.

参考文献中间体

合成目标

【1】 Ohnishi, H.; Kosuzume, H.; Mizota, M.; Suzuki, Y.; Mochida, E. (Mochida Pharmaceutical Co., Ltd.); Cephalosporin derivs.. AU 8654876; AU 8655860; EP 0197409; EP 0359291; JP 1987077392; JP 1987161793; JP 1987167784; US 4840945; US 5001121; WO 8605786 .
【2】 Kusakabe, S.; Kosuzume, H.; Kato, K.; Shiihara, T.; Murakami, K.; Yamada, H.; Ishigura, J.; Oikawa, Y.; Mochizuki, H.; Antibacterial and pharmacokinetic properties of M1. J Antibiot 1988, 41, 3, 377.
【3】 Prous, J.; Castaner, J.; M-14659. Drugs Fut 1988, 13, 12, 1047.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(IX)	23009	2-([2-(benzhydryloxy)-1-[3,4-bis(acetoxy)phenyl]-2-oxoethoxy]imino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid	C₄₉H₃₉N₃O₉S	详情	详情
(X)	23010	benzhydryl 7-[([(7R)-7-amino-2-[(benzhydryloxy)carbonyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl)sulfanyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate	C₄₁H₃₄N₆O₅S₂	详情	详情
(XI)	23011	benzhydryl 7-[([(7R)-7-([2-([2-(benzhydryloxy)-1-[3,4-bis(acetoxy)phenyl]-2-oxoethoxy]imino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-2-[(benzhydryloxy)carbonyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl)sulfanyl]-5-methyl[1,2,	C₉₀H₇₁N₉O₁₃S₃	详情	详情

Extended Information