ethyl (2S)-2-amino-3-(4-bromophenyl)propanoate -Drug Synthesis Database

【结构式】

【分子编号】32547

【品名】ethyl (2S)-2-amino-3-(4-bromophenyl)propanoate

【CA登记号】

【分子式】C₁₁H₁₄BrNO₂

【分子量】272.1417

【元素组成】C 48.55% H 5.19% Br 29.36% N 5.15% O 11.76%

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：(II)

Treatment of N-Boc-4-bromo-L-phenylalanine (I) with ethanolic or methanolic HCl gave aminoester (II). Subsequent condensation of (II) with 2,6-dichlorobenzoyl chloride (III) produced amide (IV). Lithiation of 1,3-dimethoxybenzene (V) with n-butyllithium, followed by reaction with trimethyl borate and aqueous hydrolysis yielded boronic acid (VI). Suzuki coupling of bromide (IV) with boronic acid (VI) in the presence of palladium catalyst furnished biphenyl derivative (VII). Finally, hydrolysis of the ethyl ester of (VII) with LiOH provided the title carboxylic acid.

参考文献中间体

合成目标

【1】 Sircar, I.; et al.; Synthesis and SAR of N-benzoyl-L-biphenylalanine derivatives: Discovery of TR-14035, a dual alpha4beta7/alpha4beta1 integrin antagonist. Bioorg Med Chem 2002, 10, 6, 2051.
【2】 Gudmundsson, K.S.; Sircar, I.; Martin, R. (Tanabe Seiyaku Co., Ltd.); Inhibitors of alpha4 mediated cell adhesion. WO 9936393 .

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)	32546	(2S)-3-(4-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propionic acid		C₁₄H₁₈BrNO₄	详情	详情
(II)	32547	ethyl (2S)-2-amino-3-(4-bromophenyl)propanoate		C₁₁H₁₄BrNO₂	详情	详情
(III)	25087	2,6-dichlorobenzoyl chloride	4659-45-4	C₇H₃Cl₃O	详情	详情
(IV)	32548	ethyl (2S)-3-(4-bromophenyl)-2-[(2,6-dichlorobenzoyl)amino]propanoate		C₁₈H₁₆BrCl₂NO₃	详情	详情
(V)	11934	m-Dimethoxybenzene; 1,3-Dimethoxybenzene; 3-Methoxyphenyl methyl ether	151-10-0	C₈H₁₀O₂	详情	详情
(VI)	32549	2,6-dimethoxyphenylboronic acid	23112-96-1	C₈H₁₁BO₄	详情	详情
(VII)	32550	ethyl (2S)-2-[(2,6-dichlorobenzoyl)amino]-3-(2',6'-dimethoxy[1,1'-biphenyl]-4-yl)propanoate		C₂₆H₂₅Cl₂NO₅	详情	详情

Extended Information