新产品编号:1525557

Chemical Name: 1-(L-Prolyl)pyrrolidine-2-phosphonic acid bis(4-acetamidophenyl)ester hydrochloride
项目整合开发状态: Biological Testing
项目研究机构: University of Antwerp (Originator)
合成路线:The cyclocondensation of triphenylphosphite (I) with 4-(benzyloxycarbonyl-L-prolylamino)butyraldehyde (II) in hot acetic acid gives the pyrrolidinylphosphonate (III),which is deprotected by hydrogenation with H2 over Pd/C in methanol.The intermediates (I) and (II) have been obtained as follows:Phosphite (I): The acylation of 4-aminophenol (IV) with acetic acid and isobutyl chloroformate in DMF gives N-(4-hydroxyphenyl)acetamide (V),which is allowed to react with PCl3 and triethylamine in DMF yielding phosphite (I).4-(Benzyloxycarbonyl-L-prolylamino)butyraldehyde (II): The condensation of N-(benzyloxycarbonyl)-L-proline (VI) with 4-aminobutyraldehyde diethylacetal (VII) by means of isobutyl chloroformate and triethylamine in chloroform gives 4-[N-(benzyloxycarbonyl)-L-prolylamino]butyraldehyde diethylacetal (VIII),which is hydrolyzed to the target aldehyde (II) with HCl in THF.