2-hydroxy-2-(2-isopropyl-2,3-dihydro-1H-inden-5-yl)propanoic acid -Drug Synthesis Database

【结构式】

【分子编号】60963

【品名】2-hydroxy-2-(2-isopropyl-2,3-dihydro-1H-inden-5-yl)propanoic acid

【CA登记号】

【分子式】C₁₅H₂₀O₃

【分子量】248.322

【元素组成】C 72.55% H 8.12% O 19.33%

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：(V)

The Friedel-Kraft's reaction of 2-isopropylindan (I) with ethyloxalyl chloride (II) by means of AlCl3 in methylene chloride gives ethyl 2-(2-isopropyl-5-indanyl)-2-oxoacetate (III), which is hydrolyzed with NaOH in refluxing ethanol to the corresponding free acid (IV). The reaction of (IV) with methylmagnesium iodide in ether yields 2-(2-isopropyl-5-indanyl)-2-hydroxypropionic acid (V), which is dehydrated with H2SO4 in refluxing dioxane affording 2-(2-isopropyl-5-indanyl)acrylic acid (VI) (1,2,4). Finally this compound is reduced with H2 over Raney-Ni or Pd/C in methanol or dioxane

参考文献中间体

合成目标

【1】 Blancafort, P.; Serradell, M.N.; Castaner, J.; Arrigoni, Martelli, E.; Isoprofen. Drugs Fut 1981, 6, 8, 471.
【2】 Payne, T.G. (Hexachimie SA); CH 605564 .
【3】 Teulon, J,M,; et al. (Hexachimie SA); BE 824522; CA 1063618; CH 603533; CH 605567; DD 117209; DD 118271; DD 123319; DE 2504689; FR 2260334; GB 1492175; JP 76125367; JP 76125368; NL 7501518; NL 7501519; US 4069326; US 4088787; US 4182896; ZA 7500707 .
【4】 Teulon, J.M.; et al.; Antiinflammatory and analgesic diastereoisomeric derivatives of indan-5-acetic acid. J Med Chem 1978, 21, 4, 901.
【5】 Payne, T.G. (Hexachimie SA); CH 605565 .

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)	60960	2-isopropylindane		C₁₂H₁₆	详情	详情
(II)	11043	Ethyl 2-chloro-2-oxoacetate; Ethyl oxalyl chloride	4755-77-5	C₄H₅ClO₃	详情	详情
(III)	60961	ethyl 2-(2-isopropyl-2,3-dihydro-1H-inden-5-yl)-2-oxoacetate		C₁₆H₂₀O₃	详情	详情
(IV)	60962	2-(2-isopropyl-2,3-dihydro-1H-inden-5-yl)-2-oxoacetic acid		C₁₄H₁₆O₃	详情	详情
(V)	60963	2-hydroxy-2-(2-isopropyl-2,3-dihydro-1H-inden-5-yl)propanoic acid		C₁₅H₂₀O₃	详情	详情
(VI)	60964	2-(2-isopropyl-2,3-dihydro-1H-inden-5-yl)acrylic acid		C₁₅H₁₈O₂	详情	详情

Extended Information