4-methylbenzenesulfonyl azide -Drug Synthesis Database

【结构式】

【分子编号】37748

【品名】4-methylbenzenesulfonyl azide

【CA登记号】941-55-9

【分子式】C₇H₇N₃O₂S

【分子量】197.2176

【元素组成】C 42.63% H 3.58% N 21.31% O 16.23% S 16.26%

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：(II)

Diethyl diazomalonate (III) was prepared by reaction of diethyl malonate (I) with p-tosyl azide (II) in the presence of Et3N. Subsequent coupling of (II) with 4-hydroxytetrahydropyran (IV) using dirhodium tetraacetate as the catalyst afforded ether (V). Alkylation of (V) with 3-(tert-butoxycarbonylamino)propyl bromide (VI) yielded adduct (VII). Finally, hydrolysis of ester groups of (VII) employing LiOH furnished the title dicarboxylic acid lithium salt.

参考文献中间体

合成目标

【1】 Fiorentino, S.; Allegretti, M.; Mantovanini, M.; Clavenna, G.; Caselli, G.; Gandolfi, C.A. (Dompé Farmaceutici SpA); Geminal carboxylic acids and esters thereof pharmaceutical formulations containing them useful in the treatment of bone dysmetabolism. EP 0792878; US 5908863 .

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)	16829	Diethyl malonate	105-53-3	C₇H₁₂O₄	详情	详情
(II)	37748	4-methylbenzenesulfonyl azide	941-55-9	C₇H₇N₃O₂S	详情	详情
(III)	37749	diethyl 2-diazomalonate		C₇H₁₀N₂O₄	详情	详情
(IV)	37750	tetrahydro-2H-pyran-4-ol; 4-Hydroxytetrahydropyran	2081-44-9	C₅H₁₀O₂	详情	详情
(V)	37751	diethyl 2-(tetrahydro-2H-pyran-4-yloxy)malonate		C₁₂H₂₀O₆	详情	详情
(VI)	37752	tert-butyl 3-bromopropylcarbamate		C₈H₁₆BrNO₂	详情	详情
(VII)	37753	diethyl 2-[3-[(tert-butoxycarbonyl)amino]propyl]-2-(tetrahydro-2H-pyran-4-yloxy)malonate		C₂₀H₃₅NO₈	详情	详情

Extended Information