methyl 5-methoxy-1-benzofuran-2-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】50910

【品名】methyl 5-methoxy-1-benzofuran-2-carboxylate

【CA登记号】

【分子式】C₁₁H₁₀O₄

【分子量】206.198

【元素组成】C 64.07% H 4.89% O 31.04%

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：(XI)

Ether cleavage of methyl 5-methoxybenzofuran-2-carboxylate (XI) was achieved by treatment with aluminum chloride and ethanethiol to provide phenol (XII). Subsequent Mitsunobu coupling of the resulting phenol derivative (XII) with N-(2-hydroxyethyl)morpholine (XIII) gave ether (XIV). Basic hydrolysis of the ester group provided acid (XV), which was further coupled with the intermediate amine (X) to yield amide (XVI). Finally, oxidation of the alcohol function of (XVI) under Swern conditions gave rise to the title ketone derivative.

参考文献中间体

合成目标

【1】 Bondinell, W.E.; Desjarlais, R.L.; Yamashita, D.S.; Veber, D.F. (GlaxoSmithKline Inc.); Protease inhibitors. WO 9959526 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(X)	50909	(2S)-2-amino-N-[(1S)-2-hydroxy-1-methyl-3-([2-[3-(2-pyridinyl)phenyl]acetyl]amino)propyl]-4-methylpentanamide		C₂₃H₃₂N₄O₃	详情	详情
(XI)	50910	methyl 5-methoxy-1-benzofuran-2-carboxylate		C₁₁H₁₀O₄	详情	详情
(XII)	50911	methyl 5-hydroxy-1-benzofuran-2-carboxylate		C₁₀H₈O₄	详情	详情
(XIII)	12856	4-(2-Hydroxyethyl)morpholine; 2-(4-Morpholinyl)-1-ethanol; N-(2-Hydroxyethyl)morpholine	622-40-2	C₆H₁₃NO₂	详情	详情
(XIV)	50912	methyl 5-[2-(4-morpholinyl)ethoxy]-1-benzofuran-2-carboxylate		C₁₆H₁₉NO₅	详情	详情
(XV)	50913	5-[2-(4-morpholinyl)ethoxy]-1-benzofuran-2-carboxylic acid		C₁₅H₁₇NO₅	详情	详情
(XVI)	50914	N-[(1S)-1-([[(1S)-2-hydroxy-1-methyl-3-([2-[3-(2-pyridinyl)phenyl]acetyl]amino)propyl]amino]carbonyl)-3-methylbutyl]-5-[2-(4-morpholinyl)ethoxy]-1-benzofuran-2-carboxamide		C₃₈H₄₇N₅O₇	详情	详情

Extended Information