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【结 构 式】 
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【分子编号】57375 【品名】methyl (2R)-2-[(3,5-dimethylbenzoyl)amino]-3-(4-nitrophenyl)propanoate 【CA登记号】 |
【 分 子 式 】C19H20N2O5 【 分 子 量 】356.37828 【元素组成】C 64.04% H 5.66% N 7.86% O 22.45% |
合成路线1
该中间体在本合成路线中的序号：(IV)Esterification of 4-nitro-D-phenylalanine (I) with HCl/MeOH provides the amino ester (II). This is subsequently acylated with 3,5-dimethylbenzoyl chloride (III), yielding amide (IV). Alkylation of amide (IV) by means of iodomethane and NaH affords the N-methyl amide (V). The nitro group of (V) is then reduced to amine (VI) by catalytic hydrogenation over Pd/C. Clauson-Kaas condensation of amine (VI) with 2,5-dimethoxytetrahydrofuran (VII) leads to the pyrrole derivative (VIII). The methyl ester function of (VIII) is then hydrolyzed with LiOH to provide the carboxylic acid (IX).
| 【1】 Ksander, G.M.; Kukkola, P.J.; Robinson, L.A. (Novartis AG); N-aroylamino acid amides as endothelin inhibitors. EP 0821670; JP 1999505522; WO 9633170 . |
| 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) | 57380 | (2R)-2-amino-3-(4-nitrophenyl)propanoic acid | C9H10N2O4 | 详情 | 详情 | |
| (II) | 57381 | methyl (2R)-2-amino-3-(4-nitrophenyl)propanoate | C10H12N2O4 | 详情 | 详情 | |
| (III) | 57374 | 3,5-dimethylbenzoyl chloride | C9H9ClO | 详情 | 详情 | |
| (IV) | 57375 | methyl (2R)-2-[(3,5-dimethylbenzoyl)amino]-3-(4-nitrophenyl)propanoate | C19H20N2O5 | 详情 | 详情 | |
| (V) | 57376 | methyl (2R)-2-[(3,5-dimethylbenzoyl)(methyl)amino]-3-(4-nitrophenyl)propanoate | C20H22N2O5 | 详情 | 详情 | |
| (VI) | 57377 | methyl (2R)-3-(4-aminophenyl)-2-[(3,5-dimethylbenzoyl)(methyl)amino]propanoate | C20H24N2O3 | 详情 | 详情 | |
| (VII) | 12132 | 2,5-Dimethoxytetrahydrofuran; 5-Methoxytetrahydro-2-furanyl methyl ether | 696-59-3 | C6H12O3 | 详情 | 详情 |
| (VIII) | 57378 | methyl (2R)-2-[(3,5-dimethylbenzoyl)(methyl)amino]-3-[4-(1H-pyrrol-1-yl)phenyl]propanoate | C24H26N2O3 | 详情 | 详情 | |
| (IX) | 57379 | (2R)-2-[(3,5-dimethylbenzoyl)(methyl)amino]-3-[4-(1H-pyrrol-1-yl)phenyl]propanoic acid | C23H24N2O3 | 详情 | 详情 |