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【结 构 式】 
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【分子编号】11004 【品名】(4R)-6-Cyano-5-(methoxycarbonyl)-2-methyl-4-(3-nitrophenyl)-1,4-dihydro-3-pyridinecarboxylic acid 【CA登记号】 |
【 分 子 式 】C16H13N3O6 【 分 子 量 】343.29584 【元素组成】C 55.98% H 3.82% N 12.24% O 27.96% |
合成路线1
该中间体在本合成路线中的序号：(Va)2) The optical isomers of nilvidapine have also been synthesized: The selective hydrolysis of nilvadipine (I) with formic acid gives the monocarboxylic acid (II), which is treated with (-)-cinconidine, yielding the corresponding salt (IV) as a diastereomeric mixture, which is separated by fractional crystallization to give, after hydrolysis with HCl, 2-cyano-3-(methoxycarbonyl)-6-methyl-4(R)-(3-nitrophenyl)-1,4-dihydropy ridine-5-carboxylic acid (Va) and 2-cyano-3-(methoxycarbonyl)-6-methyl-4(S)-(3-nitrophenyl)-1,4-dihydropy ridine-5-carboxylic acid (Vb) as pure optical isomers. Both compounds are esterified by conversion to the corresponding acyl chlorides with PCl5 and esterification with isopropyl alcohol.
| 【1】 Okumura, K.; Satoh, Y.; Shiokawa, Y.; Studies on nilvadipine. IV. Synthesis of deuterated and optically active isopropyl 2-cyano-3-methoxycarbonyl-4-(3-nitrophenyl)-6-methyl-1,4-dihydropyridine-5-carboxylate (nilvadipine). Chem Pharm Bull 1994, 42, 4, 950. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (Va) | 11004 | (4R)-6-Cyano-5-(methoxycarbonyl)-2-methyl-4-(3-nitrophenyl)-1,4-dihydro-3-pyridinecarboxylic acid | C16H13N3O6 | 详情 | 详情 | |
| (Vb) | 11005 | (4S)-6-Cyano-5-(methoxycarbonyl)-2-methyl-4-(3-nitrophenyl)-1,4-dihydro-3-pyridinecarboxylic acid | C16H13N3O6 | 详情 | 详情 | |
| (I) | 11001 | 5-(tert-butyl) 3-methyl 2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydro-3,5-pyridinedicarboxylate | C20H21N3O6 | 详情 | 详情 | |
| (II) | 11002 | 6-Cyano-5-(methoxycarbonyl)-2-methyl-4-(3-nitrophenyl)-1,4-dihydro-3-pyridinecarboxylic acid | C16H13N3O6 | 详情 | 详情 | |
| (IV) | 11003 | 6-Cyano-5-(methoxycarbonyl)-2-methyl-4-phenyl-1,4-dihydro-3-pyridinecarboxylic acid | C16H14N2O4 | 详情 | 详情 |