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【结 构 式】

【分子编号】32189

【品名】2-oxo-5-vinyl-3-pyrrolidinecarboxylic acid

【CA登记号】

【 分 子 式 】C7H9NO3

【 分 子 量 】155.1534

【元素组成】C 54.19% H 5.85% N 9.03% O 30.94%

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:(V)

This compound can be prepared in two different ways: 1) The reaction of 1,4-dichloro-2-butene (I) with diethyl malonate (II) by means of sodium ethoxide in refluxing ethanol gives 1,1-bis(ethoxycarbonyl)-2-vinylcyclopropane (III), which by reaction with ammonia gas in DMF at 120 C is converted into 3-carboxamido-5-vinyl-2-pyrrolidone (IV). Finally, this compound is treated with concentrated HCl in refluxing acetic acid. 2) The treatment of (IV) with sodium ethoxide in refluxing ethanol gives 3-carboxy-5-vinyl-2-pyrrolidone (V), which is decarboxylated by treatment with refluxing acetic acid to afford 5-vinyl-2-pyrrolidone (VI). The bromination of (VI) with Br2 in CCl4 yields 5-(1,2-dibromoethyl)-2-pyrrolidone (VII), which by treatment with Na in liquid NH3 in a pressure vessel at 25 C is converted into 4-aminohex-5-inoic acid (VIII). Finally, this compound is partially reduced with H2 over a suitable catalyst.

1 Gittos, M.W.; Leterre, G.J.; Process for making 4-aminohex-5-enoic acid. FR 2415630; GB 2013205; JP 54112860; US 4178463 .
2 Metcalf, B.W.; Jung, M.; Olefinic derivatives of amino acids. US 4039549 .
3 Metcalf, B.W.; Jung, M.; Olefinic derivatives of amino acids. CA 1077487; FR 2304329; GB 1472525; JP 76125320; US 3960927 .
4 Blancafort, P.; Paton, D.M.; Serradell, M.N.; Castaner, J.; RMI-71,754. Drugs Fut 1981, 6, 6, 363.
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) 32186 (E)-1,4-dichloro-2-butene 110-57-6 C4H6Cl2 详情 详情
(II) 16829 Diethyl malonate 105-53-3 C7H12O4 详情 详情
(III) 32187 Diethyl 2-vinyl-1,1-cyclopropanedicarboxylate C11H16O4 详情 详情
(IV) 32188 2-Oxo-5-vinyl-3-pyrrolidinecarboxamide; 3-Carboxamido-5-vinyl-2-pyrrolidone 71107-19-2 C7H10N2O2 详情 详情
(V) 32189 2-oxo-5-vinyl-3-pyrrolidinecarboxylic acid C7H9NO3 详情 详情
(VI) 32190 5-Vinyl-2-pyrrolidinone C6H9NO 详情 详情
(VII) 32191 5-(1,2-dibromoethyl)-2-pyrrolidinone C6H9Br2NO 详情 详情
(VIII) 32192 4-amino-5-hexynoic acid C6H9NO2 详情 详情
Extended Information