methyl 2-[3-(3-bromopropoxy)phenyl]acetate -Drug Synthesis Database

【结构式】

【分子编号】58568

【品名】methyl 2-[3-(3-bromopropoxy)phenyl]acetate

【CA登记号】

【分子式】C₁₂H₁₅BrO₃

【分子量】287.1533

【元素组成】C 50.19% H 5.27% Br 27.83% O 16.72%

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：(XII)

In a solution-phase synthesis, 2,2-diphenylethylamine (VI) was reductively condensed with 2-chloro-3-(trifluoromethyl)benzaldehyde (VIII) using a polymer-supported borohydride resin to give the secondary amine (X). Mitsunobu coupling of methyl 3-hydroxyphenylacetate (XI) with 3-bromo-1-propanol (IV) afforded the bromopropyl ether (XII). Condensation of bromide (XII) with amine (X) in refluxing acetonitrile furnished amino ester (XIII). This was finally hydrolyzed with LiOH to the title carboxylic acid.

参考文献中间体

合成目标

【1】 Willson, T.M.; Collins, J.L.; Maloney, P.R.; Fivush, A.M.; Stewart, E.L. (GlaxoSmithKline plc); Chemical cpds.. WO 0224632 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	12573	3-Bromo-1-propanol; 3-Bromopropanol	627-18-9	C₃H₇BrO	详情	详情
(VI)	38962	2,2-diphenylethylamine; 2,2-diphenyl-1-ethanamine	3963-62-0	C₁₄H₁₅N	详情	详情
(VIII)	58564	2-chloro-3-trifluoromethyl benzaldehyde	93118-03-7	C₈H₄ClF₃O	详情	详情
(X)	58566	N-[2-chloro-3-(trifluoromethyl)benzyl]-2,2-diphenyl-1-ethanamine; N-[2-chloro-3-(trifluoromethyl)benzyl]-N-(2,2-diphenylethyl)amine		C₂₂H₁₉ClF₃N	详情	详情
(XI)	58567	methyl 2-(3-hydroxyphenyl)acetate		C₉H₁₀O₃	详情	详情
(XII)	58568	methyl 2-[3-(3-bromopropoxy)phenyl]acetate		C₁₂H₁₅BrO₃	详情	详情
(XIII)	58569	methyl 2-(3-{3-[[2-chloro-3-(trifluoromethyl)benzyl](2,2-diphenylethyl)amino]propoxy}phenyl)acetate		C₃₄H₃₃ClF₃NO₃	详情	详情

Extended Information