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【结 构 式】

【分子编号】16099

【品名】tert-butyl (2S,4S)-2-[[(aminosulfonyl)(tert-butoxycarbonyl)amino]methyl]-4-sulfanyltetrahydro-1H-pyrrole-1-carboxylate

【CA登记号】

【 分 子 式 】C15H29N3O6S2

【 分 子 量 】411.54388

【元素组成】C 43.78% H 7.1% N 10.21% O 23.33% S 15.58%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(VII)

A new synthesis of S-4661 has been reported: The protection of trans-4-hydroxy-L-proline with tert-butoxycarbonyl anhydride gives N-(tert-butoxycarbonyl)-4(R)-hydroxy-L-proline (II), which is successively treated with ethyl chloroformate, mesylated with mesyl chloride and reduced with NaBH4 yielding (2S,4R)-1-(tert-butoxycarbonyl)-2-(hydroxymethyl)-4-(methanesulfonyloxy)pyrrolidine (III). The reaction of (III) with potassium thioacetate affords Compound (IV), which is condensed with N-(tert-butoxycarbonyl)sulfamide (V) by means of diethyl azodicarboxylate and triphenylphosphine to give the protected pyrrolidinesulfamide (VI). The deacetylation of (VI) with sodium methoxide yields (2S,4S)-1-(tert-butoxycarbonyl)-2-[N-(tert-butoxycarbonyl)-N-sulfamoylaminomethyl]-4-sulfanylpyrrolidine (VII), which is then condensed with (1R,5S,6S)-2-(diphenoxyphosphoryloxy)-6-[1(R)-hydroxyethyl]-1-methyl-1-carba-2-penem-3-carboxylic acid diphenylmethyl ester (VIII) by means of diisopropylethylamine to afford the protected final product (IX). Finally, this compound is deprotected with AlCl3 in anisole.

1 Motokawa, K.; Nishitani, Y.; Iso, Y.; Kii, M.; Irie, T.; Sendo, Y.; Iwaki, T.; Synthesis and modification of a novel 1beta-methyl carbapenem antibiotic, S-4661. J Antibiot 1996, 49, 5, 478.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 14489 (2S,4R)-4-hydroxytetrahydro-1H-pyrrole-2-carboxylic acid; L-Hydroxyproline 51-35-4 C5H9NO3 详情 详情
(II) 16094 (2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid;1-(tert-butoxycarbonyl)-4®-hydroxy-L-proline;(2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxytetrahydro-1H-pyrrole-2-carboxylic acid 16094 C10H17NO5 详情 详情
(III) 16095 tert-butyl (2S,4R)-2-(hydroxymethyl)-4-[(methylsulfonyl)oxy]tetrahydro-1H-pyrrole-1-carboxylate C11H21NO6S 详情 详情
(IV) 16096 tert-butyl (2S,4S)-4-(acetylsulfanyl)-2-(hydroxymethyl)tetrahydro-1H-pyrrole-1-carboxylate C12H21NO4S 详情 详情
(V) 16097 tert-butyl 2,2-dioxo-2lambda(6)-diazathiane-1-carboxylate 148017-28-1 C5H12N2O4S 详情 详情
(VI) 16098 tert-butyl (2S,4S)-4-(acetylsulfanyl)-2-[[(aminosulfonyl)(tert-butoxycarbonyl)amino]methyl]tetrahydro-1H-pyrrole-1-carboxylate C17H31N3O7S2 详情 详情
(VII) 16099 tert-butyl (2S,4S)-2-[[(aminosulfonyl)(tert-butoxycarbonyl)amino]methyl]-4-sulfanyltetrahydro-1H-pyrrole-1-carboxylate C15H29N3O6S2 详情 详情
(VIII) 16100 benzhydryl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C35H32NO8P 详情 详情
(IX) 16101 benzhydryl (4R,5S,6S)-3-[[(3S,5S)-5-[[(aminosulfonyl)(tert-butoxycarbonyl)amino]methyl]-1-(tert-butoxycarbonyl)pyrrolidinyl]sulfanyl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C38H50N4O10S2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(VII)

 

1 Zhang AY, Zhu XY, Yuan ZD.2006.Synthesis of doripenem. Chin J Pharmaceuticals, 37: 361~363
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(III) 67084 (4S)-1-tert-butyl 2-methyl 4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate   C12H21NO7S 详情 详情
(I) 67082 (4S)-4-hydroxypyrrolidine-2-carboxylic acid   C5H9NO3 详情 详情
(II) 67083 (4S)-methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride   C6H11NO3.HCl 详情 详情
(IV) 16095 tert-butyl (2S,4R)-2-(hydroxymethyl)-4-[(methylsulfonyl)oxy]tetrahydro-1H-pyrrole-1-carboxylate C11H21NO6S 详情 详情
(V) 16096 tert-butyl (2S,4S)-4-(acetylsulfanyl)-2-(hydroxymethyl)tetrahydro-1H-pyrrole-1-carboxylate C12H21NO4S 详情 详情
(VI) 16098 tert-butyl (2S,4S)-4-(acetylsulfanyl)-2-[[(aminosulfonyl)(tert-butoxycarbonyl)amino]methyl]tetrahydro-1H-pyrrole-1-carboxylate C17H31N3O7S2 详情 详情
(VII) 16099 tert-butyl (2S,4S)-2-[[(aminosulfonyl)(tert-butoxycarbonyl)amino]methyl]-4-sulfanyltetrahydro-1H-pyrrole-1-carboxylate C15H29N3O6S2 详情 详情
(VIII) 16100 benzhydryl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C35H32NO8P 详情 详情
(IX) 16101 benzhydryl (4R,5S,6S)-3-[[(3S,5S)-5-[[(aminosulfonyl)(tert-butoxycarbonyl)amino]methyl]-1-(tert-butoxycarbonyl)pyrrolidinyl]sulfanyl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C38H50N4O10S2 详情 详情
(X) 67085 4-nitrobenzyl 6-(1-hydroxyethyl)-4-methyl-7-oxo-3-((5-((sulfamoylamino)methyl)pyrrolidin-3-yl)thio)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate   C22H29N5O8S2 详情 详情
Extended Information