4-bromobutyric acid -Drug Synthesis Database

【结构式】

【分子编号】40604

【品名】4-bromobutyric acid

【CA登记号】2623-87-2

【分子式】C₄H₇BrO₂

【分子量】167.00238

【元素组成】C 28.77% H 4.22% Br 47.85% O 19.16%

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：

Esterification of alcohol (XXXII) with either 4-bromobutyric acid and DCC or 4-bromobutyryl chloride gave rise to bromoester (XL). Then displacement of the bromine atom of (XL) with silver dibenzylphosphate yielded phosphate ester (XLI). The title compound was then obtained by hydrogenolysis of the benzyl ester groups of (XLI) over Pd/C.

参考文献中间体

合成目标

【1】 Girijavallabhan, V.M.; et al.; Sch 59884, a water-soluble prodrug of Sch 56592 for intravenous formulations. 39th Intersci Conf Antimicrob Agents Chemother (Sept 26 1999, San Francisco) 1999, Abst F1932.
【2】 Bennett, F.; Girijavallabhan, V.M.; Patel, N.M.; Ganguly, A.; Saksena, A.K. (Schering Corp.); Tetrahydrofuran phosphate- and hydroxy esters, as prodrugs for the corresponding antifungal agent. EP 1027349; WO 9915522 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	40603	silver(1+) bis(benzyloxy)(oxo)phosphoranolate		C₁₄H₁₄AgO₄P	详情	详情
	40604	4-bromobutyric acid	2623-87-2	C₄H₇BrO₂	详情	详情
	40605	4-bromobutanoyl chloride	927-58-2	C₄H₆BrClO	详情	详情
(XXXII)	34850	4-[4-[4-(4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy]phenyl)-1-piperazinyl]phenyl]-2-[(1S,2S)-1-ethyl-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one		C₃₇H₄₂F₂N₈O₄	详情	详情
(XL)	34854	(1S,2S)-2-(4-[4-[4-(4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy]phenyl)-1-piperazinyl]phenyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-1-methylbutyl 4-bromobutanoate		C₄₁H₄₇BrF₂N₈O₅	详情	详情
(XLI)	34855	(1S,2S)-2-(4-[4-[4-(4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy]phenyl)-1-piperazinyl]phenyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-1-methylbutyl 4-[[bis(benzyloxy)phosphoryl]oxy]butanoate		C₅₅H₆₁F₂N₈O₉P	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

The esterification of paracetamol (I) with 4-bromobutyric acid (II) by means of DCC and DMAP in DMF gives the corresponding ester (III), which is finally treated with AgNO3 in hot acetonitrile to yield the target nitrate ester.

参考文献中间体

合成目标

【1】 Del Soldato, P. (NicOx SA); Pharmaceutical cpds.. EP 1252133; WO 0112584 .

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)	21611	4'-Hydroxyacetanilide;4-Acetamidophenol;N-Acetyl-4-aminophenol;Paracetamol;Acetaminophen;p-Hydroxyacetanilide; Paracetamol; N-(4-hydroxyphenyl)acetamide	103-90-2	C₈H₉NO₂	详情	详情
(II)	40604	4-bromobutyric acid	2623-87-2	C₄H₇BrO₂	详情	详情
(III)	56709	4-(acetylamino)phenyl 4-bromobutanoate		C₁₂H₁₄BrNO₃	详情	详情

Extended Information