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【结 构 式】 
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【药物名称】Divalproex sodium, Valproate semisodium, Abbott-50711, CerebSyrup, Epival, Depakote, D閜akine Chrono 【化学名称】2-Propylpentanoic acid sodium salt (2:1) 【CA登记号】76584-70-8 【 分 子 式 】C16H31NaO4 【 分 子 量 】310.41287 |
【开发单位】Abbott (Originator), Andrx (Not Determined), Sanofi-synthélabo (Not Determined), Ohta (Licensee), Fujisawa (Distributor) 【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Antiepileptic Drugs, Antimigraine Drugs, Bipolar Disorder, Treatment of, Migraine, Prophylactic Treatment of, Mood Disorders, Treatment of, NEUROLOGIC DRUGS, PSYCHOPHARMACOLOGIC DRUGS |
合成路线1
By reaction of valproic acid (I) with NaOH in water - acetonitrile (II).
合成路线2
This compound has been obtained by two different ways: 1) The reaction of dipropylcarbinol (I) with HBr gives 4-bromoheptane (II), which is treated with KCN to yield 2-propylpentanenitrile (III). Finally, this compound is hydrolyzed to the target compound with NaOH or with H2SO4. 2) The condensation of cyanacetic acid ethyl ester (IV) with propyl bromide (V) by means of sodium propoxide in propanol gives crude dipropylcyanaacetic acid ethyl ester, which, without isolation, is hydrolyzed with NaOH in hot water yielding dipropylcyanacetic acid (VI). The decarboxylation of (VI) at 140-190 C affords the previously reported 2-propylpentanenitrile (III).
| 【1】 Walles, M.; et al.; Z Physiolog Chem 1947, 282, 2, 137. |
| 【2】 Grain, C.; Chignac, M.; Pigerol, C. (Labaz); Process for the preparation of acetonitrile deriv.. US 4155929 . |
| 【3】 Chignac, M.; Grain, C.; Pigerol, C. (Labaz); Process for preparing an acetonitrile deriv.. GB 1522450 . |
| 【4】 Pigerol, C.; Grain, C.; Chignac, M. (Labaz); Process for preparing acetic acid derivs.. GB 1529786 . |
| 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) | 34880 | 4-heptanol | 589-55-9 | C7H16O | 详情 | 详情 |
| (II) | 34881 | 4-bromoheptane | 998-93-6 | C7H15Br | 详情 | 详情 |
| (III) | 34882 | 2-propylpentanenitrile | 13310-75-3 | C8H15N | 详情 | 详情 |
| (IV) | 11877 | Cyanoacetic acid ethyl ester; Ethyl 2-cyanoacetate; Ethyl cyanoacetate; Ethyl isocyanacetate | 105-56-6 | C5H7NO2 | 详情 | 详情 |
| (V) | 28721 | 1-bromobutane | 109-65-9 | C4H9Br | 详情 | 详情 |
| (VI) | 34883 | 2-cyano-2-propylpentanoic acid | C9H15NO2 | 详情 | 详情 |