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【结 构 式】

【分子编号】18306

【品名】3-(3,4-dimethoxyphenyl)-beta-alanine

【CA登记号】

【 分 子 式 】C11H15NO4

【 分 子 量 】225.24444

【元素组成】C 58.66% H 6.71% N 6.22% O 28.41%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(III)

Condensation of 3,4-dimethoxybenzaldehyde (I) with malonic acid (II) in the presence of ammonium acetate afforded 3-amino-arylpropionic acid (III), which was esterified with MeOH and SOCl2 to give (IV). Finally, condensation with tetrafluorophthalic anhydride (V) in refluxing AcOH provided the target phthalimide.

1 Muller, G.W.; Shire, M.G.; Wong, L.M.; Corral, L.G.; Patterson, R.T.; Chen, Y.; Stirling, D.I.; Thalidomide analogs and PDE4 inhibition. Bioorg Med Chem Lett 1998, 8, 19, 2669.
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) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(III) 18306 3-(3,4-dimethoxyphenyl)-beta-alanine C11H15NO4 详情 详情
(IV) 18307 methyl 3-amino-3-(3,4-dimethoxyphenyl)propanoate hydrochloride C12H18ClNO4 详情 详情
(V) 18308 4,5,6,7-tetrafluoro-2-benzofuran-1,3-dione; Tetrafluorophthalic anhydride 652-12-0 C8F4O3 详情 详情

合成路线2

该中间体在本合成路线中的序号:(II)

Condensation of veratraldehyde (I) with malonic acid and ammonium acetate in refluxing EtOH afforded 3-amino-3-(3,4-dimethoxyphenyl)propionic acid (II). The N-phthaloyl group was introduced in (II) by treatment with N-carbethoxyphthalimide (III) in the presence of Na2CO3. The resulting phthalimido acid (IV) was converted to the title amide via activation with carbonyl diimidazole, followed by treatment with ammonium hydroxide.

1 Fernandez-Martinez, E.; et al.; Effects of thalidomide and 3-phthalimido-3-(3,4-dimethoxyphenyl)-propanamide on bile duct obstruction-induced cirrhosis in the rat. Drug Dev Res 2001, 54, 4, 209.
2 Muller, G.W.; Shire, M.G.; Wong, L.M.; Corral, L.G.; Patterson, R.T.; Chen, Y.; Stirling, D.I.; Thalidomide analogs and PDE4 inhibition. Bioorg Med Chem Lett 1998, 8, 19, 2669.
3 Muller, G.W.; et al.; Structural modifications of thalidomide produce analogs with enhanced tumor necrosis factor inhibitory activity. J Med Chem 1996, 39, 17, 3238.
4 Muller, G.W. (Celgene Corp.); Ring closure of N-phthaloylglutamines. EP 1004572; EP 1004580; US 5463063; WO 9501348 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
12963 Malonic acid 141-82-2 C3H4O4 详情 详情
(I) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(II) 18306 3-(3,4-dimethoxyphenyl)-beta-alanine C11H15NO4 详情 详情
(III) 10283 ethyl 1,3-dioxo-1,3-dihydro-2H-isoindole-2-carboxylate; N-Carbethoxyphthalimide 22509-74-6 C11H9NO4 详情 详情
(IV) 37235 3-(3,4-dimethoxyphenyl)-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propionic acid C19H17NO6 详情 详情
Extended Information