4-dodecylbenzenesulfonyl azide -Drug Synthesis Database

【结构式】

【分子编号】33042

【品名】4-dodecylbenzenesulfonyl azide

【CA登记号】

【分子式】C₁₈H₂₉N₃O₂S

【分子量】351.51328

【元素组成】C 61.5% H 8.32% N 11.95% O 9.1% S 9.12%

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：(VI)

Azetidineacetic acid derivative (I) was activated with 1,1'-carbonyldiimidazole and then condensed with p-nitrobenzyl malonate magnesium salt (II) to afford ketoester (III). Desilylation of (III) with methanolic HCl then gave alcohol (IV). Dodecylbenzenesulfonyl azide (VI) was prepared by treatment of sulfonyl chloride (V) with NaN3. Reaction of (IV) with sulfonyl azide (VI) provided diazo ester (VII). Ring closure of (VII) in the presence of rhodium diacetate in hot cyclohexane, followed by condensation with diphenylphosphoric chloride furnished carbapenem phosphate (VIII).

参考文献中间体

合成目标

【1】 Lin, Y.-I.; Bitha, P.; Sakya, S.; Strohmeyer, T.W.; Bush, K. (American Cyanamid Co.); Novel 2-thiosubstd. carbapenems. CA 2118961; EP 0617036; JP 1994321948; US 5602118 .

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)	30029	(2R)-2-[(2S,3S)-3-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-4-oxoazetidinyl]propionic acid		C₁₄H₂₇NO₄Si	详情	详情
(II)	33039	magnesium 2-(4-nitrobenzyl)malonate		C₁₀H₇MgNO₆	详情	详情
(III)	33040	4-nitrobenzyl (4R)-4-[(2R,3S)-3-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-4-oxoazetidinyl]-3-oxopentanoate		C₂₃H₃₄N₂O₇Si	详情	详情
(IV)	22573	4-nitrobenzyl 4-[(2R,3S)-3-[(1R)-1-hydroxyethyl]-4-oxoazetidinyl]-3-oxopentanoate		C₁₇H₂₀N₂O₇	详情	详情
(V)	33041	4-dodecylbenzenesulfonyl chloride		C₁₈H₂₉ClO₂S	详情	详情
(VI)	33042	4-dodecylbenzenesulfonyl azide		C₁₈H₂₉N₃O₂S	详情	详情
(VII)	30150	(3S,4R)-3-((1R)-1-Hydroxyethyl)-4[(1R)-1-methyl-3-diazo-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl]azetidin-2-one	137391-68-5	C₁₇H₁₈N₄O₇	详情	详情
(VIII)	13224	4-nitrobenzyl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	90776-59-3	C₂₉H₂₇N₂O₁₀P	详情	详情

Extended Information