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【结 构 式】 
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【分子编号】21923 【品名】methyl 5-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-methoxybenzoate 【CA登记号】 |
【 分 子 式 】C13H11NO5S 【 分 子 量 】293.30008 【元素组成】C 53.24% H 3.78% N 4.78% O 27.27% S 10.93% |
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)1) The Knoevenagel condensation of aldehyde (I) with rhodanine (II) using NH4OAc and AcOH afforded benzylidene- thiazolidine (III). The methyl ester group of (III) was hydrolyzed with HCl in AcOH, and the resulting carboxylic acid (IV) was coupled to 4-(trifluoromethyl)benzylamine (V) in the presence of diethyl phosphorocyanidate and Et3N to produce amide (VI). Subsequent hydrogenation of the olefinic double bond of (VI) over Pd/C provided the target benzylthiazolidine.
| 【1】 Nomura, M.; et al.; (3-Substituted benzyl)thiazolidine-2,4-diones as structurally new antihyperglycemic agents. Bioorg Med Chem Lett 1999, 9, 4, 533. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 42235 | Diethyl phosphorocyanidate; Diethyl cyanophosphonate; Cyanophosphonic acid diethyl ester; Diethyl phosphoryl cyanide; DEPC | 2942-58-7 | C5H10NO3P | 详情 | 详情 | |
| (I) | 21921 | methyl 5-formyl-2-methoxybenzoate | C10H10O4 | 详情 | 详情 | |
| (II) | 10883 | 1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione | 2295-31-0 | C3H3NO2S | 详情 | 详情 |
| (III) | 21923 | methyl 5-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-methoxybenzoate | C13H11NO5S | 详情 | 详情 | |
| (IV) | 21924 | 5-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-methoxybenzoic acid | C12H9NO5S | 详情 | 详情 | |
| (V) | 21925 | [4-(trifluoromethyl)phenyl]methanamine; 4-(trifluoromethyl)benzylamine | 3300-51-4 | C8H8F3N | 详情 | 详情 |
| (VI) | 21926 | 5-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-methoxy-N-[4-(trifluoromethyl)benzyl]benzamide | C20H15F3N2O4S | 详情 | 详情 |
Extended Information