5-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-methoxybenzoic acid -Drug Synthesis Database

【结构式】

【分子编号】21933

【品名】5-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-methoxybenzoic acid

【CA登记号】

【分子式】C₁₂H₁₁NO₅S

【分子量】281.28908

【元素组成】C 51.24% H 3.94% N 4.98% O 28.44% S 11.4%

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：(XIII)

2) An alternative method starting from aniline (VII) employed the Meerwein arylation of methyl acrylate (IX) with the intermediate diazonium salt (VIII) in the presence of cuprous oxide. The resulting bromoester (X) was cyclized with thiourea (XI) in Et2O, followed by hydrolysis with HCl in sulfolane to afford (XIII). Finally, acid (XIII) was coupled to benzylamine (V) in the presence of (EtO)2POCN and Et3N.

参考文献中间体

合成目标

【1】 Nomura, M.; et al.; (3-Substituted benzyl)thiazolidine-2,4-diones as structurally new antihyperglycemic agents. Bioorg Med Chem Lett 1999, 9, 4, 533.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	42235	Diethyl phosphorocyanidate; Diethyl cyanophosphonate; Cyanophosphonic acid diethyl ester; Diethyl phosphoryl cyanide; DEPC	2942-58-7	C₅H₁₀NO₃P	详情	详情
(V)	21925	[4-(trifluoromethyl)phenyl]methanamine; 4-(trifluoromethyl)benzylamine	3300-51-4	C₈H₈F₃N	详情	详情
(VII)	21927	methyl 5-amino-2-methoxybenzoate		C₉H₁₁NO₃	详情	详情
(VIII)	21928	methyl 5-(1lambda(5)-diazynyl)-2-methoxybenzoate		C₉H₁₀N₂O₃	详情	详情
(IX)	14156	methyl acrylate	96-33-3	C₄H₆O₂	详情	详情
(X)	21930	methyl 5-(2-bromo-3-methoxy-3-oxopropyl)-2-methoxybenzoate		C₁₃H₁₅BrO₅	详情	详情
(XI)	10180	Thiourea	62-56-6	CH₄N₂S	详情	详情
(XII)	21932	methyl 5-[(2-imino-4-oxo-1,3-thiazolidin-5-yl)methyl]-2-methoxybenzoate		C₁₃H₁₄N₂O₄S	详情	详情
(XIII)	21933	5-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-methoxybenzoic acid		C₁₂H₁₁NO₅S	详情	详情

Extended Information