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【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.

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 CAS号 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