【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% |
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 |