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【结 构 式】

【分子编号】27629

【品名】methyl 4-(acetamido)-2-methyl-2,3-dihydro-1-benzofuran-7-carboxylate

【CA登记号】

【 分 子 式 】C13H15NO4

【 分 子 量 】249.26644

【元素组成】C 62.64% H 6.07% N 5.62% O 25.67%

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:(I)

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
Extended Information