2-(bromomethyl)-1-benzothiophene -Drug Synthesis Database

【结构式】

【分子编号】64465

【品名】2-(bromomethyl)-1-benzothiophene

【CA登记号】

【分子式】C₉H₇BrS

【分子量】227.12458

【元素组成】C 47.59% H 3.11% Br 35.18% S 14.12%

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：(IV)

D-Glutamic acid (I) is treated with SOCl2 in EtOH to produce ethyl D-pyroglutamate (II). Further protection of (II) with di-tert-butyl dicarbonate yields the N-Boc pyroglutamate (III) (1). The lithiated derivative of (III) is alkylated with 2-(bromomethyl)benzothiophene (IV) to afford the trans alkylated isomer (V). Basic hydrolysis of (V) produces the N-Boc amino diacid (VI). Then, acidic Boc group cleavage in (VI), followed by treatment of the resultant hydrochloride salt with propylene oxide in MeOH leads to the free aminoacid (1,2).

参考文献中间体

合成目标

【1】 De Dios, A.; Prieto, L.; Martin, J.A.; Rubio, A.; Ezquerra, J.; Tebbe, M.; López de Uralde, B.; Martín, J.; Sánchez, A.; LeTourneu, D.L.; McGee, J.E.; Boylan, C.; Parr, T.R.; Smith, M.C.; 4-Substituted D-glutamic acid analogues: The first potent inhibitors of glutamate racemase (MurI) enzyme with antibacterial activity. J Med Chem 2002, 45, 20, 4559.
【2】 Martin, J.A.; Ezquerra-Carrera, J.; Tebbe, M.J.; De Dios, A.; Prieto, L.; McGee, J.E.; Rubio-Esteban, A.; Smith, M.C. (Eli Lilly and Company); Chemical cpds.. WO 0214261 .

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)	54708	(R)-(-)-Glutamic acid; (R)-2-Aminoglutaric acid; D-(+)-Glutamic acid; D-2-Aminoglutaric acid; D-glutamic acid	6893-26-1	C₅H₉NO₄	详情	详情
(II)	64464	ethyl (2R)-5-oxo-2-pyrrolidinecarboxylate		C₇H₁₁NO₃	详情	详情
(III)	43914	1-(tert-butyl) 2-ethyl (2S)-5-oxo-1,2-pyrrolidinedicarboxylate	144978-35-8	C₁₂H₁₉NO₅	详情	详情
(IV)	64465	2-(bromomethyl)-1-benzothiophene		C₉H₇BrS	详情	详情
(V)	64466	1-(tert-butyl) 2-ethyl (2R,4R)-4-(1-benzothiophen-2-ylmethyl)-5-oxo-1,2-pyrrolidinedicarboxylate		C₂₁H₂₅NO₅S	详情	详情
(VI)	64467	(2R,4R)-2-(1-benzothiophen-2-ylmethyl)-4-[(tert-butoxycarbonyl)amino]pentanedioic acid		C₁₉H₂₃NO₆S	详情	详情

Extended Information