GW-500580X

Chemical Name: 5-[(E)-(2,4-Dioxothiazolidin-5-ylidenemethyl)-N-[1(S)-phenylethyl]-2-propoxybenzamide
项目整合开发状态: Preclinical
项目研究机构: GlaxoSmithKline (Originator)
合成路线: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.