N-((6R,7R)-2-[(benzhydryloxy)carbonyl]-7-methoxy-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-en-7-yl)-2-[4-[(4-methoxybenzyl)oxy]phenyl]-3-oxo-beta-alanine -Drug Synthesis Database

【结构式】

【分子编号】39539

【品名】N-((6R,7R)-2-[(benzhydryloxy)carbonyl]-7-methoxy-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-en-7-yl)-2-[4-[(4-methoxybenzyl)oxy]phenyl]-3-oxo-beta-alanine

【CA登记号】

【分子式】C₄₁H₃₈N₆O₁₀S

【分子量】806.85316

【元素组成】C 61.03% H 4.75% N 10.42% O 19.83% S 3.97%

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：(XXVId)

1) By condensation of benzhydryl (6R,7R)-7-amino-7-methoxy-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (XXIV) with alpha-diphenylmethoxycarbonyl-alpha-(p-hydroxyphenyl)acetic acid (XXVa) by means of Et3N and oxalyl chloride in methylene chloride gives the 7-[alpha-diphenylmethoxycarbonyl-alpha-(p-hydroxyphenyl)acetamido]-7alpha-methoxy compound (XXVIa). Finally, all the protecting groups of (XXVIa) are eliminated by treatment with trifluoroacetic acid in anisole. 2) Compound (XXIV) can also be condensed with alpha-(p-benzyloxyphenyl)malonic acid monobenzyl ester (XXVb) by means of Et3N and oxalyl chloride in methylene chloride yielding the 7beta-[alpha-(p-benzyloxyphenyl)-alpha-benzyloxycarbonylacetamido]-7alpha-methoxy compound (XXVIb), which is hydrolyzed with trifluoroacetic acid in anisole. 3) Compound (XXIV) can also be condensed with alpha-(p-methoxybenzyl)oxycarbonyl-alpha-[p-(p-methoxybenzyl)oxyphenylacetic acid (XXVc) by means of Et3N and oxalyl chloride in methylene chloride giving the corresponding derivative (XXVIc), which can be hydrolyzed with trifluoroacetic acid in anisole. 4) Finally, compound (XXIV) can also be condensed with p-(p-methoxybenzyloxy)phenylmalonic acid (XXVd) by means of Et3N and oxalyl chloride in methylene chloride affording compound (XXVId), which is hydrolyzed with trifluoroacetic in anisole. 5) Compound (XXIV) can also be condensed with alpha-diphenylmethoxycarbonyl-p-(p-methoxybenzyl)oxyphenylacetic acid (XXVe) by means of Et3N and oxalyl chloride in methylene chloride affording the corresponding derivative (XXVIe), which is hydrolyzed with trifluoroacetic acid in anisole.

参考文献中间体

合成目标

【1】 Serradell, M.N.; Blancafort, P.; Castaner, J.; S-6059. Drugs Fut 1979, 4, 9, 667.
【2】 Narisada, M.; Nagata, W. (Shionogi & Co. Ltd.); Arylmalonamido-1-oxadethiacephalosporins. DE 2713370; US 4138486 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXVa)	39531	3-(benzhydryloxy)-2-(4-hydroxyphenyl)-3-oxopropionic acid	C₂₂H₁₈O₅	详情	详情
(XXVb)	39532	3-(benzyloxy)-2-[4-(benzyloxy)phenyl]-3-oxopropionic acid	C₂₃H₂₀O₅	详情	详情
(XXVc)	39533	3-[(4-methoxybenzyl)oxy]-2-[4-[(4-methoxybenzyl)oxy]phenyl]-3-oxopropionic acid	C₂₅H₂₄O₇	详情	详情
(XXVd)	39534	2-[4-[(4-methoxybenzyl)oxy]phenyl]malonic acid	C₁₇H₁₆O₆	详情	详情
(XXVe)	39535	3-(benzhydryloxy)-2-[4-[(4-methoxybenzyl)oxy]phenyl]-3-oxopropionic acid	C₃₀H₂₆O₆	详情	详情
(XXVIa)	39536	benzhydryl (6R,7R)-7-[[3-(benzhydryloxy)-2-(4-hydroxyphenyl)-3-oxopropanoyl]amino]-7-methoxy-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	C₄₆H₄₀N₆O₉S	详情	详情
(XXVIb)	39537	benzhydryl (6R,7R)-7-([3-(benzyloxy)-2-[4-(benzyloxy)phenyl]-3-oxopropanoyl]amino)-7-methoxy-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	C₄₇H₄₂N₆O₉S	详情	详情
(XXVIc)	39538	benzhydryl (6R,7R)-7-methoxy-7-[(3-[(4-methoxybenzyl)oxy]-2-[4-[(4-methoxybenzyl)oxy]phenyl]-3-oxopropanoyl)amino]-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	C₄₉H₄₆N₆O₁₁S	详情	详情
(XXVId)	39539	N-((6R,7R)-2-[(benzhydryloxy)carbonyl]-7-methoxy-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-en-7-yl)-2-[4-[(4-methoxybenzyl)oxy]phenyl]-3-oxo-beta-alanine	C₄₁H₃₈N₆O₁₀S	详情	详情
(XXVIe)	39540	benzhydryl (6R,7R)-7-[(3-(benzhydryloxy)-2-[4-[(4-methoxybenzyl)oxy]phenyl]-3-oxopropanoyl)amino]-7-methoxy-3-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	C₅₄H₄₈N₆O₁₀S	详情	详情
(XXIV)	37782	(1R)-3-chloro-1-phenyl-1-propanol	C₉H₁₁ClO	详情	详情

Extended Information