2-[2-(4-Methylphenyl)-2-oxoethyl]acrylic acid -Drug Synthesis Database

【结构式】

【分子编号】12892

【品名】2-[2-(4-Methylphenyl)-2-oxoethyl]acrylic acid

【CA登记号】

【分子式】C₁₂H₁₂O₃

【分子量】204.22548

【元素组成】C 70.57% H 5.92% O 23.5%

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：(III)

The Friedel-Crafts condensation of toluene (I) with itaconic anhydride (2-methylenesuccinic anhydride) (II) by means of AlCl3 in methylene chloride or 1,2-dichloroethane gives 3-(4-methylbenzoyl)-2-methylenepropionic acid (III), which is then treated with thioacetic acid (IV) and K2CO3 in DMF/water.

参考文献中间体

合成目标

【1】 Onodera, A.; Tomisawa, K.; Noguchi, T.; Yokomori, S.; A practical procedure for the synthesis of esonarimod, (R,S)-2-acetylthiomethyl-4-(4-methylphenyl)-4-oxobutanoic acid, an antirheumatic agent (Part 1). Chem Pharm Bull 2002, 50, 10, 1407.
【2】 Mealy, N.; Castaner, J.; KE-298. Drugs Fut 1996, 21, 7, 691.
【3】 Tomisawa, K.; Kameo, K.; Matsunaga, T.; Saito, S.; Sota, K. (Taisho Pharmaceutical Co., Ltd.); Benzoylpropionic acid derivs., their use and pharmaceutical compsns. EP 0164101; ES 8603818; JP 1985258160 .
【4】 Tomisawa, K.; Kameo, K.; Matsunaga, Y.; Saito, H.; Sodu, H. (Taisho Pharmaceutical Co., Ltd.); 2-Acylthiomethyl-3-benzoylpropionic acid derivs. JP 1987132825 .
【5】 Kameo, K.; Ogawa, K.; Takeshita, K.; Nakaike, S.; Tomisawa, K.; Sota, K.; Studies on antirheumatic agents: 3-Benzoylpropionic acid derivatives. Chem Pharm Bull 1988, 36, 6, 2050-60.

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)	12890	Toluene	108-88-3	C₇H₈	详情	详情
(II)	12891	3-Methylenedihydro-2,5-furandione; Itaconic anhydride	2170-03-8	C₅H₄O₃	详情	详情
(III)	12892	2-[2-(4-Methylphenyl)-2-oxoethyl]acrylic acid		C₁₂H₁₂O₃	详情	详情
(IV)	12893	Ethanethioic S-acid		C₂H₄OS	详情	详情

Extended Information