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【结 构 式】 
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【分子编号】55618 【品名】(2S)-2-({[3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydro-4-pyridinyl]carbonyl}amino)pentanedioic acid 【CA登记号】 |
【 分 子 式 】C19H26N2O9 【 分 子 量 】426.42352 【元素组成】C 53.52% H 6.15% N 6.57% O 33.77% |
合成路线1
该中间体在本合成路线中的序号：(IV)The dihydropyridine-4-carboxylic acid derivative (I) was activated as the pentafluorophenyl ester (II) using pentafluorophenol and DCC. Coupling of the active ester (II) with glutamic acid (III) furnished the N-acyl glutamic acid (IV). Alternatively, (IV) was obtained by coupling of glutamic acid (III) with the pyridine acid (I) via activation with DCC/HOBt. Diacid (IV) was finally treated with NaOH to produce the corresponding disodium salt.
| 【1】 Biseniex, E.A.; Uldrikis, Y.R.; Dubur, G.Y.; Veveris, M.M.; Kimenis, A.A.; Ivanov, E.V. (Latvian Institute of Organic Synthesis); 2-(2,6-Dimethyl-3,5-diethoxycarbonyl-1,4-dihydropyridine-4-carboxamide) glutaric acid its disodium salt and method of their preparation. US 4485239 . |
| 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) | 55616 | 3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydro-4-pyridinecarboxylic acid | C14H19NO6 | 详情 | 详情 | |
| (II) | 55612 | ethyl (4R)-3-[2-(2,3-dihydro-1H-inden-2-yl)acetyl]-1,3-thiazolidine-4-carboxylate | C17H21NO3S | 详情 | 详情 | |
| (III) | 12005 | L-2-Amino propane dicarboxylic acid; (-)-2-Aminoglutaric acid; L-2-Aminopentanoic acid; L-Glutamic acid | 56-86-0 | C5H9NO4 | 详情 | 详情 |
| (IV) | 55618 | (2S)-2-({[3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydro-4-pyridinyl]carbonyl}amino)pentanedioic acid | C19H26N2O9 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IV)In a related method for the preparation of (IV), acid (I) was activated as the mixed anhydride (V) using isobutyl chloroformate. Coupling of anhydride (V) with the silyl ester (VI), prepared from glutamic acid (III) and hexamethyldisilazane, provided amide (IV).
| 【1】 Biseniex, E.A.; Uldrikis, Y.R.; Dubur, G.Y.; Veveris, M.M.; Kimenis, A.A.; Ivanov, E.V. (Latvian Institute of Organic Synthesis); 2-(2,6-Dimethyl-3,5-diethoxycarbonyl-1,4-dihydropyridine-4-carboxamide) glutaric acid its disodium salt and method of their preparation. US 4485239 . |
| 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) | 55616 | 3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydro-4-pyridinecarboxylic acid | C14H19NO6 | 详情 | 详情 | |
| (III) | 12005 | L-2-Amino propane dicarboxylic acid; (-)-2-Aminoglutaric acid; L-2-Aminopentanoic acid; L-Glutamic acid | 56-86-0 | C5H9NO4 | 详情 | 详情 |
| (IV) | 55618 | (2S)-2-({[3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydro-4-pyridinyl]carbonyl}amino)pentanedioic acid | C19H26N2O9 | 详情 | 详情 | |
| (V) | 55619 | C19H27NO8 | 详情 | 详情 | ||
| (VI) | 55620 | bis(trimethylsilyl) (2S)-2-aminopentanedioate | C11H25NO4Si2 | 详情 | 详情 |