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【结 构 式】 
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【药物名称】 【化学名称】5(R)-(Methoxymethyl)-3-(1H-pyrrol-1-yl)oxazolidin-2-one 【CA登记号】 【 分 子 式 】C9H12N2O3 【 分 子 量 】196.20759 |
【开发单位】Università degli Studi "La Sapienza" (Originator), Università degli Studi di Salerno (Originator), Università degli Studi di Siena (Originator) 【药理作用】Antidepressants, Mood Disorders, Treatment of, PSYCHOPHARMACOLOGIC DRUGS, MAO-A Inhibitors |
合成路线1
Condensation of benzyl carbazate (I) with 2,5-dimethoxytetrahydrofuran (II) affords the N-benzyloxycarbonyl aminopyrrole (III). The lithiated derivative of (III) is condensed with (R)-glycidyl butyrate (IV) to furnish the chiral oxazolidinone (V). Alcohol (V) is converted to the corresponding mesylate (VI) with methanesulfonyl chloride and triethylamine. Finally, nucleophilic displacement of mesylate (VI) with sodium methoxide affords the target methyl ether.
| 【1】 Massa, S.; Befani, O.; Esposito, M.; Sbardella, g.; Mai, A.; Turini, P.; Giovannini, V.; Mondovi, B.; 3-(1H-Pyrrol-1-yl)-2-oxazolidinones as reversible, highly potent, and selective inhibitors of monoamine oxidase type A. J Med Chem 2002, 45, 6, 1180. |
| 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) | 36108 | benzyl 1-hydrazinecarboxylate | 5331-43-1 | C8H10N2O2 | 详情 | 详情 |
| (II) | 12132 | 2,5-Dimethoxytetrahydrofuran; 5-Methoxytetrahydro-2-furanyl methyl ether | 696-59-3 | C6H12O3 | 详情 | 详情 |
| (III) | 57806 | benzyl 1H-pyrrol-1-ylcarbamate | C12H12N2O2 | 详情 | 详情 | |
| (IV) | 18385 | (2R)oxiranylmethyl butyrate;(R)-glycidyl butyrate | 60456-26-0 | C7H12O3 | 详情 | 详情 |
| (V) | 57807 | (5R)-5-(hydroxymethyl)-3-(1H-pyrrol-1-yl)-1,3-oxazolidin-2-one | C8H10N2O3 | 详情 | 详情 | |
| (VI) | 57808 | [(5R)-2-oxo-3-(1H-pyrrol-1-yl)-1,3-oxazolidin-5-yl]methyl methanesulfonate | C9H12N2O5S | 详情 | 详情 |