methyl 2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]acetate -Drug Synthesis Database

【结构式】

【分子编号】46879

【品名】methyl 2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]acetate

【CA登记号】

【分子式】C₁₃H₁₃NO₅S

【分子量】295.31596

【元素组成】C 52.87% H 4.44% N 4.74% O 27.09% S 10.86%

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：(X)

Alkylation of 5-(4-hydroxybenzyl)-3-tritylthiazolidine-2,4-dione (VII) with methyl bromoacetate (VIII) in the presence of cesium carbonate gave rise to the aryloxy acetate (IX). Subsequent cleavage of the N-trityl protecting group of (IX) was achieved by treatment with HOAc in aqueous dioxan at 80 C. The resulting ester (X) was finally condensed with phenylenediamine (VI) to produce the target benzimidazole.

参考文献中间体

合成目标

【2】 Fujita, T.; Fujiwara, T.; Izumi, T. (Sankyo Co., Ltd.); Hydrochloride of fused-heterocycle cpd.. EP 1180519; JP 2001039976; US 2002111373; WO 0071540 .
【1】 Fujita, T.; Wada, K.; Oguchi, M.; Yanagisawa, H.; Fujimoto, K.; Fujiwara, T.; Horikoshi, H.; Yoshioka, T. (Sankyo Co., Ltd.); Benzimidazole derivs., their preparation and their therapeutic use. CA 2177858; EP 0745600; JP 1997295970; JP 2000001487; US 5886014 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VI)	46877	N-(2-amino-5-methoxyphenyl)-N-methylamine; 4-methoxy-N(2)-methyl-1,2-benzenediamine		C₈H₁₂N₂O	详情	详情
(VII)	18803	5-(4-hydroxybenzyl)-3-trityl-1,3-thiazolidine-2,4-dione		C₂₉H₂₃NO₃S	详情	详情
(VIII)	12309	methyl 2-bromoacetate; methyl bromoacetate	96-32-2	C₃H₅BrO₂	详情	详情
(IX)	46878	methyl 2-[4-[(2,4-dioxo-3-trityl-1,3-thiazolidin-5-yl)methyl]phenoxy]acetate		C₃₂H₂₇NO₅S	详情	详情
(X)	46879	methyl 2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]acetate		C₁₃H₁₃NO₅S	详情	详情

Extended Information