3-[(4-oxopentanoyl)oxy]-2-phenylpropionic acid -Drug Synthesis Database

【结构式】

【分子编号】24320

【品名】3-[(4-oxopentanoyl)oxy]-2-phenylpropionic acid

【CA登记号】

【分子式】C₁₄H₁₆O₅

【分子量】264.27804

【元素组成】C 63.63% H 6.1% O 30.27%

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：(II)

1) The reaction of N1-(4-chlorobenzoyl)-N1-(4-methoxyphenyl)hydrazine (I) [the starting material for the synthesis of indomethacin], with d,l-(2-carboxyethyl-2-phenyl)-4-oxopentanoate (II) under the conditions of Fischer indole synthesis by means of 100% phosphoric acid in toluene at 100 C. d,l-(2-Carboxyethyl-2-phenyl)-4-oxopentanoate (II) is obtained hy treatment of d,l-tropic acid with levulinic acid chloride.

参考文献中间体

合成目标

【1】 Grimova, J.; Rabek, V.; Roubal, Z.; Fisnerova, L.; Pharmacologically interesting derivatives of indomethacin. Cesk Farm 1977, 26, 277.
【2】 Fisnerova, L.; Nemecek, O.; Method of producing 2-phenyl-2-carboxyethyl ester of 1-p-chlorobenzoyl-5-methoxy-2-methyl-3-indolyl acetic acid. CS 194284 .
【3】 Sletzinger, M.; Chemerda, J.M.; Summit, G.G. (Merck & Co., Inc.); N-acyl-phenylhydrazine sulfamic acids and salts thereof. DE 1643462; DE 1643463; DE 1768016; DE 1770022; FR 1540724; FR 1540725; GB 1161270; GB 1173986 .
【4】 Fisnerova, L.; Nemecek, O.; Method of producing 2-phenyl-2-carboxyethyl ester of levulinic acid. CS 194283 .
【5】 Nemecek, O.; Fisnerova, L.; Grimova, J.; Roubal, Z. (SPOFA - United Pharmaceutical Works); 2-Phenyl-2-carboxyethyl 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetate and process for preparation thereof. US 4136194 .
【6】 Fisnerova, L.; Tropesin. Drugs Fut 1986, 11, 9, 779.

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)	24319	4-chloro-N-(4-methoxyphenyl)benzohydrazide		C₁₄H₁₃ClN₂O₂	详情	详情
(II)	24320	3-[(4-oxopentanoyl)oxy]-2-phenylpropionic acid		C₁₄H₁₆O₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

2) The reaction of indomethacin (III) with thionyl chloride in hot toluene gives the corresponding acyl chloride (IV), which is then condensed with tropic acid (V) in refluxing toluene containing pyridine to afford title compound.

参考文献中间体

合成目标

【1】 Nemecek, O.; Fisnerova, L.; Grimova, J.; Roubal, Z. (SPOFA - United Pharmaceutical Works); 2-Phenyl-2-carboxyethyl 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetate and process for preparation thereof. US 4136194 .
【2】 Fisnerova, L.; Tropesin. Drugs Fut 1986, 11, 9, 779.
【3】 Fisnerova, L.; et al.; Pharmacologically interesting indomethacin derivatives. Cesk Farm 1977, 26, 6, 227-31.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(III)	22930	2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid	C₁₉H₁₆ClNO₄	详情	详情
(IV)	24074	2-[(3,4-dihydro-2H-thiochromen-8-yloxy)methyl]oxirane	C₁₂H₁₄O₂S	详情	详情
(V)	24320	3-[(4-oxopentanoyl)oxy]-2-phenylpropionic acid	C₁₄H₁₆O₅	详情	详情

Extended Information