(2S,3S,5S,8S,9S,10S,13S,14S,17S)-2-ethoxy-3-hydroxy-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)hexadecahydro-11H-cyclopenta[a]phenanthren-11-one oxime -Drug Synthesis Database

【结构式】

【分子编号】39211

【品名】(2S,3S,5S,8S,9S,10S,13S,14S,17S)-2-ethoxy-3-hydroxy-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)hexadecahydro-11H-cyclopenta[a]phenanthren-11-one oxime

【CA登记号】

【分子式】C₂₅H₄₁NO₅

【分子量】435.60428

【元素组成】C 68.93% H 9.49% N 3.22% O 18.36%

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：(III)

The ketalization of 2beta-ethoxy-3alpha-hydroxy-5alpha-pregnane-11,20-dione (I) with ethylene glycol (A) by means of p-toluenesulfonic acid in refluxing benzene gives the corresponding 20,20-ethylenedioxy derivative (II), which is treated with hydroxylamine hydrochloride and NaOH refluxing ethanol to yield 20,20-ethylenedioxy-2beta-ethoxy-3alpha-hydroxy-5alpha-pregnan-11-one 11-oxime (III). The reduction of (III) with Na in refluxing propanol (B) affords 11alpha-amino-20,20-ethylenedioxy-2beta-ethoxy-3alpha-hydroxy-5alpha-pregnan (IV), which is finally methylated with methyl iodide and K2CO3 or with formaldehyde and formic acid, and hydrolyzed with HCl or H2SO4.

参考文献中间体

合成目标

【1】 Philips, G.H.; Ewan, G.; DE 2715078 .
【2】 Hillier, K.; Castaner, J.; Blancafort, P.; Serradell, M.N.; Minaxolone. Drugs Fut 1980, 5, 12, 614.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(AI)	11295	Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol	107-21-1	C₂H₆O₂	详情	详情
(B)	29338	1-propanol	71-23-8	C₃H₈O	详情	详情
(I)	39209	(2S,3S,5S,8S,9S,10S,13S,14S,17S)-17-acetyl-2-ethoxy-3-hydroxy-10,13-dimethylhexadecahydro-11H-cyclopenta[a]phenanthren-11-one		C₂₃H₃₆O₄	详情	详情
(II)	39210	(2S,3S,5S,8S,9S,10S,13S,14S,17S)-2-ethoxy-3-hydroxy-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)hexadecahydro-11H-cyclopenta[a]phenanthren-11-one		C₂₅H₄₀O₅	详情	详情
(III)	39211	(2S,3S,5S,8S,9S,10S,13S,14S,17S)-2-ethoxy-3-hydroxy-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)hexadecahydro-11H-cyclopenta[a]phenanthren-11-one oxime		C₂₅H₄₁NO₅	详情	详情
(IV)	39212	(2S,3S,5S,8S,9S,10S,11R,13S,14S,17S)-11-amino-2-ethoxy-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-ol		C₂₅H₄₃NO₄	详情	详情

Extended Information