5-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-propoxybenzoic acid -Drug Synthesis Database

【结构式】

【分子编号】58383

【品名】5-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-propoxybenzoic acid

【CA登记号】

【分子式】C₁₄H₁₃NO₅S

【分子量】307.32696

【元素组成】C 54.72% H 4.26% N 4.56% O 26.03% S 10.43%

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)

5-Formylsalicylic acid (I) is protected by esterification with H2SO4/MeOH to give the methyl ester (II). After alkylation of the phenolic hydroxyl group of (II) with propyl bromide, the resultant ortho-propoxy benzoate ester (III) is hydrolyzed to carboxylic acid (IV) with LiOH in aqueous THF. Condensation of the aldehyde-acid (IV) with 2,4-thiazolidinedione (V) in the presence of morpholine leads to the benzylidene thiazolidinedione (VI). Activation of the carboxyl group of (VI) with oxalyl chloride gives rise to the corresponding acid chloride (VII), which is then condensed with (S)-alpha-methylbenzylamine (VIII) to furnish the target amide.

参考文献中间体

合成目标

【1】 Allen, S.H.; Pfohl, J.L.; Wallace, E.; Truax, J.F.; Worley, J.K.; Townsend, C.; Peat, A.J.; Garrido, D.M.; McKay, C.; Aryl 1,3-thiazolidine-2,4-diones acting as KATP channel agonists as a class of potent antidiabetic agents. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 364.

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)	32357	5-Formylsalicylic acid; 5-formyl-2-hydroxybenzoic acid	616-76-2	C₈H₆O₄	详情	详情
(II)	58380	ethyl 5-formyl-2-hydroxybenzoate		C₁₀H₁₀O₄	详情	详情
(III)	58381	ethyl 5-formyl-2-propoxybenzoate		C₁₃H₁₆O₄	详情	详情
(IV)	58382	5-formyl-2-propoxybenzoic acid		C₁₁H₁₂O₄	详情	详情
(V)	10883	1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione	2295-31-0	C₃H₃NO₂S	详情	详情
(VI)	58383	5-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-propoxybenzoic acid		C₁₄H₁₃NO₅S	详情	详情
(VII)	58384	5-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-propoxybenzoyl chloride		C₁₄H₁₂ClNO₄S	详情	详情
(VIII)	20042	(1S)-1-phenyl-1-ethanamine; (1S)-1-phenylethylamine		C₈H₁₁N	详情	详情

Extended Information