ethyl 2-(2,4-bis{[4-(methyloxy)phenyl]carbonyl}-1H-pyrrol-1-yl)acetate -Drug Synthesis Database

【结构式】

【分子编号】64033

【品名】ethyl 2-(2,4-bis{[4-(methyloxy)phenyl]carbonyl}-1H-pyrrol-1-yl)acetate

【CA登记号】

【分子式】C₂₄H₂₃NO₆

【分子量】421.44976

【元素组成】C 68.4% H 5.5% N 3.32% O 22.78%

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：(V)

Friedel-Crafts acylation of 3-(p-methoxybenzoyl)pyrrole (I) with p-methoxybenzoyl chloride (II) gives rise to diketone (III). Subsequent alkylation of pyrrole (III) with ethyl bromoacetate (IV) in the presence of NaH and tris[(2-methoxyethoxy)ethyl]amine (TDA) furnishes the pyrrolylacetate (V). Finally, saponification of the ethyl ester group of (V) affords the target carboxylic acid.

参考文献中间体

合成目标

【1】 Nicolaou, I.; Demopoulos, V.J.; Substituted pyrrol-1-ylacetic acids that combine aldose reductase enzyme inhibitory activity and ability to prevent the nonenzymatic irreversible modification of proteins from monosaccharides. J Med Chem 2003, 46, 3, 417.

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)	64031	[4-(methyloxy)phenyl](1H-pyrrol-3-yl)methanone		C₁₂H₁₁NO₂	详情	详情
(II)	22071	2-[1,2-bis[[(E)-(2,6-dichloro-4-methoxyphenyl)methylidene]amino]-2-(2-hydroxyphenyl)ethyl]phenol		C₃₀H₂₄Cl₄N₂O₄	详情	详情
(III)	64032	[5-(4-methoxybenzoyl)-1H-pyrrol-3-yl](4-methoxyphenyl)methanone		C₂₀H₁₇NO₄	详情	详情
(IV)	16640	Ethyl 2-bromoacetate; Ethyl bromoacetate	105-36-2	C₄H₇BrO₂	详情	详情
(V)	64033	ethyl 2-(2,4-bis{[4-(methyloxy)phenyl]carbonyl}-1H-pyrrol-1-yl)acetate		C₂₄H₂₃NO₆	详情	详情

Extended Information