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【结 构 式】 
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【分子编号】22986 【品名】3-(3,4-dihydroxyphenyl)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-hydroxypropionic acid 【CA登记号】 |
【 分 子 式 】C17H13NO7 【 分 子 量 】343.29276 【元素组成】C 59.48% H 3.82% N 4.08% O 32.62% |
合成路线1
该中间体在本合成路线中的序号：(VI)The condensation of 3,4-dimethoxybenzaldehyde (I) with glycine (II) by means of KOH in hot methanol gives racemic threo-3-(3,4-dimethoxyphenyl)serine (III), which is acylated with N-(ethoxycarbonyl)phthalimide (IV) by means of Na2CO3 in water yielding the corresponding N-phthaloyl derivative (V). The reaction of (V) with AlCl3 and ethyl mercaptan in dichloromethane affords N-phthaloyl-3-(3,4-dihydroxyphenyl)serine (VI), which is deprotected with hydrazine in refluxing ethanol to racemic threo-3-(3,4-dihydroxyphenyl)serine (VII). The resolution of the racemic form (VII) is performed through its benzyloxy derivative.
| 【1】 Ohashi, N.; Nagata, S.; Ishimuzi, K.; Katsube, J. (Sumitomo Pharmaceuticals Co., Ltd.); Process for the production of optically active thr. EP 0024210; US 4319040 . |
| 【2】 Ohashi, N.; Nagata, S.; Ishizumi, K. (Sumitomo Pharmaceuticals Co., Ltd.); Process for producing 3-(3,4-dihydroxyphenyl)serin. EP 0128684; US 4562263 . |
| 【3】 Castaner, J.; Prous, J.; L-threo-DOPS. Drugs Fut 1987, 12, 5, 433. |
| 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) | 18304 | 3,4-Dimethoxybenzaldehyde; Veratraldehyde | 120-14-9 | C9H10O3 | 详情 | 详情 |
| (II) | 20436 | glycine | 56-40-6 | C2H5NO2 | 详情 | 详情 |
| (III) | 22983 | 3-hydroxy-3,4-dimethoxyphenylalanine | C11H15NO5 | 详情 | 详情 | |
| (IV) | 10283 | ethyl 1,3-dioxo-1,3-dihydro-2H-isoindole-2-carboxylate; N-Carbethoxyphthalimide | 22509-74-6 | C11H9NO4 | 详情 | 详情 |
| (V) | 22985 | 3-(3,4-dimethoxyphenyl)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-hydroxypropionic acid | C19H17NO7 | 详情 | 详情 | |
| (VI) | 22986 | 3-(3,4-dihydroxyphenyl)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-hydroxypropionic acid | C17H13NO7 | 详情 | 详情 |