(2R,5S)-3,5-dimethyl-2-(3-pyridinyl)-1,3-thiazolan-4-one -Drug Synthesis Database

【结构式】

【分子编号】16684

【品名】(2R,5S)-3,5-dimethyl-2-(3-pyridinyl)-1,3-thiazolan-4-one

【CA登记号】

【分子式】C₁₀H₁₂N₂OS

【分子量】208.28416

【元素组成】C 57.67% H 5.81% N 13.45% O 7.68% S 15.4%

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：(VII)

Methylation of methyl (+)-lactate (I) followed by thioacetylation and acidic hydrolysis affords (-)-thiolactic acid (IV). Reaction of 3-pyridinecarboxyaldehyde (V) with methylamine in toluene under the azeotropic condition provides the imine (VI), which when condensed with (IV) affords (+)-cis-3,5-dimethyl-2-(3-pyridyl)thiazolidin-4-one (VII). Treatment of (VII) with aqueous HCl/isopropanol results in the precipitation of SM-12502.

参考文献中间体

合成目标

【1】 Koike, H.; Natsume, Y.; Tojo, S.; Morooka, S.; SM-12502. Drugs Fut 1995, 20, 2, 153.

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)	11591	methyl (2R)-2-hydroxypropanoate	17392-83-5	C₄H₈O₃	详情	详情
(II)	16679	methyl (2R)-2-[(methylsulfonyl)oxy]propanoate		C₅H₁₀O₅S	详情	详情
(III)	16680	methyl (2S)-2-(acetylsulfanyl)propanoate		C₆H₁₀O₃S	详情	详情
(IV)	16681	(2S)-2-sulfanylpropionic acid		C₃H₆O₂S	详情	详情
(V)	12849	Nicotinaldehyde; 3-Pyridinecarboxaldehyde	500-22-1	C₆H₅NO	详情	详情
(VI)	16683	N-methyl-N-[(Z)-3-pyridinylmethylidene]amine; N-[(Z)-3-pyridinylmethylidene]methanamine		C₇H₈N₂	详情	详情
(VII)	16684	(2R,5S)-3,5-dimethyl-2-(3-pyridinyl)-1,3-thiazolan-4-one		C₁₀H₁₂N₂OS	详情	详情

Extended Information