2-bromo-2-(2-methylphenyl)acetic acid -Drug Synthesis Database

【结构式】

【分子编号】38983

【品名】2-bromo-2-(2-methylphenyl)acetic acid

【CA登记号】

【分子式】C₉H₉BrO₂

【分子量】229.07326

【元素组成】C 47.19% H 3.96% Br 34.88% O 13.97%

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：(XI)

In a related procedure, alkylation of 2,4-dihydroxybenzaldehyde (VI) with chloride (II) gave ether (VII). Subsequent conversion of the aldehyde group of (VII) into the desired nitrile (X) was effected by the following sequence, including formation of the corresponding oxime (VIII), dehydration with concomitant acetylation using Ac2O, and then hydrolysis of acetate (IX) using K2CO3. Alternatively, aldehyde (VII) was directly converted to nitrile (X) by reaction with hydroxylamine-O-sulfonic acid, followed by basic treatment. Racemic alpha-bromo-(2-methylphenyl)acetic acid (XI) was resolved via formation of the corresponding salt with (-)-ephedrine (XII). Hydroxy nitrile (X) was then alkylated with the chiral bromide (XII), and the resulting compound was finally converted to the corresponding sodium salt.

参考文献中间体

合成目标

【1】 Porter, B.; Astles, P.C.; Bridge, A.W.; McLay, I.M.; Van Sickle, A.P.; Walsh, R.J.A.; McCarthy, C.; Morley, A.D.; Halley, F.; Harris, N.V.; Majid, T.N.; Smith, C. (Rhône-Poulenc Rorer Ltd.); Substd. phenyl cpds. as endothelin antagonists. US 6048893; US 6124343; WO 9622978 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(II)	28617	5-(chloromethyl)-1,3-benzodioxole		C₈H₇ClO₂	详情	详情
(VI)	20094	2,4-dihydroxybenzaldehyde	95-01-2	C₇H₆O₃	详情	详情
(VII)	38979	4-(1,3-benzodioxol-5-ylmethoxy)-2-hydroxybenzaldehyde		C₁₅H₁₂O₅	详情	详情
(VIII)	38980	4-(1,3-benzodioxol-5-ylmethoxy)-2-hydroxybenzaldehyde oxime		C₁₅H₁₃NO₅	详情	详情
(IX)	38981	5-(1,3-benzodioxol-5-ylmethoxy)-2-cyanophenyl acetate		C₁₇H₁₃NO₅	详情	详情
(X)	38982	4-(1,3-benzodioxol-5-ylmethoxy)-2-hydroxybenzonitrile		C₁₅H₁₁NO₄	详情	详情
(XI)	38983	2-bromo-2-(2-methylphenyl)acetic acid		C₉H₉BrO₂	详情	详情
(XII)	38984	(2R)-2-bromo-2-(2-methylphenyl)ethanoic acid		C₉H₉BrO₂	详情	详情

Extended Information