3-(3,4-dimethoxyphenyl)-beta-alanine -Drug Synthesis Database

【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 合成路线2

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.

参考文献中间体

合成目标

【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.

参考文献中间体

合成目标

【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