N,N,N-Trimethyl-2-[(phenylsulfonyl)oxy]-1-ethanaminium chloride -Drug Synthesis Database

【结构式】

【分子编号】11333

【品名】N,N,N-Trimethyl-2-[(phenylsulfonyl)oxy]-1-ethanaminium chloride

【CA登记号】

【分子式】C₁₁H₁₈ClNO₃S

【分子量】279.78756

【元素组成】C 47.22% H 6.48% Cl 12.67% N 5.01% O 17.16% S 11.46%

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：(VIII)

An improved synthesis of ilmofosine has been reported: The reaction of 2-(hydroxymethyl)-2-propenoic acid ethyl ester (I) with PBr3 in ethyl ether gives the corresponding 2-bromomethyl derivative (II), which is condensed with hexadecylthiol (III) by means of triethylamine to afford 2-(hexadecylsulfanyl)-2-propenoic acid ethyl ester (IV). The reduction of (IV) with diisobutylaluminum hydride (DIBAL) yields 3-(hexadecylsulfanyl)-2-methylene-1-propanol (V), which is methylated with NaH and MeI to the methyl ether (VI). The hydroboration of (VI) with BH3.S(CH3)2 followed by oxidation with NaBO3 gives 3-(hexadecylsulfanyl)-2-(methoxymethyl)-1-propanol (VII), which is finally phosphorylated with PCl3 and condensed with choline p-toluenesulfonate (VIII).

参考文献中间体

合成目标

【1】 Reddy, K.C.; Byun, H.S.; Bittman, R.; Antitumor ether lipids: An improved synthesis of ilmofosine and an enantioselective synthesis of an ilmofosine analog. Tetrahedron Lett 1994, 35, 17, 2679.

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)	11327	ethyl 2-(hydroxymethyl)acrylate	10029-04-6	C₆H₁₀O₃	详情	详情
(II)	11328	ethyl 2-(bromomethyl)acrylate	17435-72-2	C₆H₉BrO₂	详情	详情
(III)	41266	1-hexadecanethiol; hexadecylhydrosulfide	2917-26-2	C₁₆H₃₄S	详情	详情
(IV)	11329	ethyl 2-[(hexadecylsulfanyl)methyl]acrylate		C₂₂H₄₂O₂S	详情	详情
(V)	11330	2-[(Hexadecylsulfanyl)methyl]-2-propen-1-ol		C₂₀H₄₀OS	详情	详情
(VI)	11331	2-[(Hexadecylsulfanyl)methyl]-2-propenyl methyl ether; 3-(Hexadecylsulfanyl)-2-(methoxymethyl)-1-propene		C₂₁H₄₂OS	详情	详情
(VII)	11332	3-(Hexadecylsulfanyl)-2-(methoxymethyl)-1-propanol		C₂₁H₄₄O₂S	详情	详情
(VIII)	11333	N,N,N-Trimethyl-2-[(phenylsulfonyl)oxy]-1-ethanaminium chloride		C₁₁H₁₈ClNO₃S	详情	详情

Extended Information