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【结 构 式】 
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【分子编号】27633 【品名】benzyl (2S)-4-(acetamido)-5-chloro-2-methyl-2,3-dihydro-1-benzofuran-7-carboxylate 【CA登记号】 |
【 分 子 式 】C19H18ClNO4 【 分 子 量 】359.80896 【元素组成】C 63.43% H 5.04% Cl 9.85% N 3.89% O 17.79% |
合成路线1
该中间体在本合成路线中的序号：(V)The hydrolysis of 4-acetamido-2-methyl-2,3-dihydrobenzofuran-7-carboxylic acid methyl ester (I) with NaOH gives the corresponding free acid (II), which is esterified with benzyl alcohol and carbonyldiimidazole (CDI) to the benzyl ester (III). Optical resolution of (III) by chiral HPLC yielded the 2(S)-isomer (IV), which is chlorinated with N-chlorosuccinomide (NCl) affords the 5-chloro derivative (V). The treatment of (V) with NaOH provides 4-amino-5-chloro-2(S)-methyl-2,3-dihydrobenzofuran-7-carboxylic acid (VI), which is condensed with the ethylamino derivative (VII) by means of CDI to give the amide (VIII). Finally, this compound is salified with fumaric acid (IX).
| 【1】 Kakigami, T.; et al.; Serotonin 5-HT4 receptor agonistic activity of the optical isomers of (±)-4-amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2,3-dihydro-2-methylbenzo[b]furan-7-carboxamide. Chem Pharm Bull 1998, 46, 6, 1039. |
| 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) | 27629 | methyl 4-(acetamido)-2-methyl-2,3-dihydro-1-benzofuran-7-carboxylate | C13H15NO4 | 详情 | 详情 | |
| (II) | 27630 | 4-(acetamido)-2-methyl-2,3-dihydro-1-benzofuran-7-carboxylic acid | C12H13NO4 | 详情 | 详情 | |
| (III) | 27631 | benzyl 4-(acetamido)-2-methyl-2,3-dihydro-1-benzofuran-7-carboxylate | C19H19NO4 | 详情 | 详情 | |
| (IV) | 27632 | benzyl (2S)-4-(acetamido)-2-methyl-2,3-dihydro-1-benzofuran-7-carboxylate | C19H19NO4 | 详情 | 详情 | |
| (V) | 27633 | benzyl (2S)-4-(acetamido)-5-chloro-2-methyl-2,3-dihydro-1-benzofuran-7-carboxylate | C19H18ClNO4 | 详情 | 详情 | |
| (VI) | 27634 | (2S)-4-amino-5-chloro-2-methyl-2,3-dihydro-1-benzofuran-7-carboxylic acid | C10H10ClNO3 | 详情 | 详情 | |
| (VII) | 19916 | 2-tetrahydro-1H-pyrrolizin-7(5H)-ylethylamine; 2-tetrahydro-1H-pyrrolizin-7(5H)-yl-1-ethanamine | C9H18N2 | 详情 | 详情 | |
| (VIII) | 27635 | (2S)-4-amino-5-chloro-2-methyl-N-[2-tetrahydro-1H-pyrrolizin-7(5H)-ylethyl]-2,3-dihydro-1-benzofuran-7-carboxamide | C19H26ClN3O2 | 详情 | 详情 | |
| (IX) | 23808 | Fumaric acid; (E)-2-butenedioic acid | 110-17-8 | C4H4O4 | 详情 | 详情 |