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【结 构 式】

【分子编号】58381

【品名】ethyl 5-formyl-2-propoxybenzoate

【CA登记号】

【 分 子 式 】C13H16O4

【 分 子 量 】236.26764

【元素组成】C 66.09% H 6.83% O 27.09%

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)

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.

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