Development of a Two-Step, Enantioselective Synthesis of an Amino Alcohol Drug Candidate

Autor:	Rossano Lucius T, Michael A. Schmidt, Vu Chi Truc, Jacob Albrecht, Andrew G. Lee, Xinhua Qian, Ehrlic Lo, Steven L. Goldberg, Emily A. Reiff, Jaan A. Pesti, Chao Hang, Kenneth J. Natalie, Animesh Goswami, Zhiwei Guo, Chenchi Wang
Rok vydání:	2015
Předmět:	chemistry.chemical_classification Drug candidate Carboxylic acid Organic Chemistry Two step Enantioselective synthesis Alcohol chemistry.chemical_compound chemistry Aldol reaction Yield (chemistry) Amide Organic chemistry Physical and Theoretical Chemistry
Zdroj:	Organic Process Research & Development. 19:1317-1322
ISSN:	1520-586X 1083-6160
Popis:	The process development and large scale synthesis for the β-hydroxyamino amide 1 is described. The route evolved from a multistep sequence utilizing a classical resolution to a two-step enantioselective process involving an enzyme-catalyzed aldol reaction and a direct amidation of a carboxylic acid. By utilizing a silicon-mediated direct amidation strategy, the route was devoid of protecting and deprotecting steps while retaining the stereochemical integrity of a highly sensitive β-hydroxyamino acid. The two-step strategy employed herein significantly improved the yield, process greenness, cycle time, and estimated cost in the production of 1.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e78e620e78b1f8852562c1c09f2eda3c https://doi.org/10.1021/acs.oprd.5b00192 Zobrazit plný text záznamu