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【结 构 式】

【分子编号】12331

【品名】Methyl 4-acetamido-2-ethoxybenzoate; methyl 4-(acetamido)-2-ethoxybenzoate

【CA登记号】59-06-3

【 分 子 式 】C12H15NO4

【 分 子 量 】237.25544

【元素组成】C 60.75% H 6.37% N 5.9% O 26.97%

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:(II)

The starting compounds (IV) and (VII) are obtained as follows: a) Methyl 4-acetylamino-2-hydroxybenzoate (I) is converted to the 2-ethoxy derivative (II) with ethyl iodide, and then chlorination of (II) with N-chlorosuccinimide followed by alkaline hydrolysis of (III) gives benzoic acid (IV). b) The reaction of 2-[(4-fluorobenzyl)amino]ethanol (V) with N-(2,3-epoxypropyl)phthalimide (VI), followed by treatment with concentrated sulfuric acid, affords intermediate (VII). The condensation of 4-Amino-5-chloro-2-ethoxybenzoic acid (IV) with 4-(4-fluorobenzyl)-2-(methylamino) morpholine (VII) by means of ethyl chloroformate and triethylamine in CHCl3 gives 4-amino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]methyl] benzamide, which is converted to mosapride citrate, by treatment with citric acid.

1 Kato, S.; Yoshida, N.; Ito, T.; Mosapride Citrate. Drugs Fut 1993, 18, 6, 513.
2 Kato, S.; Morie, T.; Hino, K.; Kon, T.; Naruto, S.; Yoshida, N.; Karasawa, T.; Matsumoto, J.; Novel benzamides as selective and potent gastrokinetic agents. 1. Synthesis and structure-activity relationships of N[4-(2-morpholinyl)alkyl]benzamides. J Med Chem 1990, 33, 5, 1406-13.
3 Kato, S.; Morie, T.; Hino, K.; Kon, T.; Naruto, S.; Yoshida, N.; Karasawa, T.; Matsumoto, J.; Novel benzamides as selective and potent gastrokinetic agents. 1. Synthesis and structure-activity relationships of N[4-(2-morpholinyl)alkyl]benzamides. J Med Chem 1990, 33, 5, 1406-13.
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) 12330 methyl 4-(acetamido)-2-hydroxybenzoate C10H11NO4 详情 详情
(II) 12331 Methyl 4-acetamido-2-ethoxybenzoate; methyl 4-(acetamido)-2-ethoxybenzoate 59-06-3 C12H15NO4 详情 详情
(III) 12332 methyl 4-(acetamido)-5-chloro-2-ethoxybenzoate C12H14ClNO4 详情 详情
(IV) 12333 4-Amino-5-chloro-2-ethoxybenzoic acid C9H10ClNO3 详情 详情
(V) 12334 2-[(4-Fluorobenzyl)amino]-1-ethanol C9H12FNO 详情 详情
(VI) 12335 2-(2-Oxiranylmethyl)-1H-isoindole-1,3(2H)-dione; N-(2,3-Epoxypropyl)phtalimide 5455-98-1 C11H9NO3 详情 详情
(VII) 12336 [4-(4-Fluorobenzyl)-1,4-oxazinan-2-yl]methylamine; [4-(4-Fluorobenzyl)-1,4-oxazinan-2-yl]methanamine; 2-Aminomethyl-4-(4-fluorobenzyl)morpholine 112914-13-3 C12H17FN2O 详情 详情
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