Wyatt C. Powell, Kelly Johnson, Peyton Tran, Ruiheng Jing, Maciej Walczak
{"title":"Improved Synthesis of Pseudoproline and DMB Dipeptide Carboxylic Acids","authors":"Wyatt C. Powell, Kelly Johnson, Peyton Tran, Ruiheng Jing, Maciej Walczak","doi":"10.1055/a-2306-9316","DOIUrl":null,"url":null,"abstract":"We report a mild method for the preparation of Fmoc-protected dipeptides containing a DMB (HMB) group or modified as pseudoprolines. To minimize the loss of the Fmoc protection, we optimized the saponification conditions and included a calcium additive that protected the other base-sensitive functionalities and improved the yield of the free acid (36-82%). The reaction requires a combination of CaCl2 and NaOH in a mixture of i-PrOH and water at room temperature.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"23 6","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2024-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synlett","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/a-2306-9316","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
We report a mild method for the preparation of Fmoc-protected dipeptides containing a DMB (HMB) group or modified as pseudoprolines. To minimize the loss of the Fmoc protection, we optimized the saponification conditions and included a calcium additive that protected the other base-sensitive functionalities and improved the yield of the free acid (36-82%). The reaction requires a combination of CaCl2 and NaOH in a mixture of i-PrOH and water at room temperature.