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

Schmidt Michael A.; Reiff Emily A.; Qian Xinhua; Hang Chao; Truc Vu Chi; Natalie Kenneth J.; Wang Chenchi; Albrecht Jacob; Lee Andrew G.; Lo Ehrlic T.; Guo Zhiwei; Goswami Animesh; Goldberg Steven; Pesti Jaan; Rossano Lucius T.

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

机译：氨基酒精候选药物的两步，对映选择性合成的开发

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The process development and large scale synthesis for the beta-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 beta-hydroxyamino acid. The two-step strategy employed herein significantly improved the yield, process greenness, cycle time, and estimated cost in the production of 1.

机译：描述了β-羟基氨基酰胺1的方法开发和大规模合成。该途径从利用经典拆分的多步骤序列发展到涉及酶催化的醛醇缩合反应和羧酸直接酰胺化的两步对映选择性过程。通过利用硅介导的直接酰胺化策略，该途径无需进行保护和脱保护步骤，同时保留了高度敏感的β-羟基氨基酸的立体化学完整性。本文采用的两步策略显着提高了1.生产的产量，工艺绿色度，循环时间和估计成本。

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《Organic process research & development》 |2015年第9期|共6页
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Schmidt Michael A.; Reiff Emily A.; Qian Xinhua; Hang Chao; Truc Vu Chi; Natalie Kenneth J.; Wang Chenchi; Albrecht Jacob; Lee Andrew G.; Lo Ehrlic T.; Guo Zhiwei; Goswami Animesh; Goldberg Steven; Pesti Jaan; Rossano Lucius T.;
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1. Development of a Two-Step, Enantioselective Synthesis of an Amino Alcohol Drug Candidate [J] . Schmidt Michael A., Reiff Emily A., Qian Xinhua, Organic process research & development . 2015,第9期

机译：氨基酒精候选药物的两步，对映选择性合成的开发
2. Synthesis of Novel H8-Binaphthol-based Chiral Receptors and Their Applications in Enantioselective Recognition of 1,2-Amino alcohols and Chirality Conversion of L-Amino acids to D-Amino acids [J] . Hyein Jung, Raju Nandhakumar, Hoe-Jin Yoon Bulletin of the Korean Chemical Society . 2010,第5期

机译：新型基于H8-联萘酚的手性受体的合成及其在1，2-氨基醇的对映选择性识别中的应用以及L-氨基酸向D-氨基酸的手性转化
3. Synthesis of Novel H8-Binaphthol-based Chiral Receptors and Their Applications in Enantioselective Recognition of 1,2-Amino alcohols and Chirality Conversion of L-Amino acids to D-Amino acids [J] . Hoe Jin Yoon, Hyein Jung, Kwan Mook Kim, Bulletin of the Korean Chemical Society . 2010,第5期

机译：新型基于H8-联萘酚的手性受体的合成及其在1，2-氨基醇的对映选择性识别和L-氨基酸向D-氨基酸的手性转化中的应用
4. Asymmetric Hydrogenation of an Amino Acid Intermediate in the Synthesis of Complex Drug Targets: From Kinetic Modeling to Process Development [C] . Daniel S. Hsieh, Dong Lin, Steve S.Y. Wang, Conference on the Catalysis of Organic Reactions . 2009

机译：复合药物靶标中氨基酸中间体的不对称氢化：从动力学建模到过程开发
5. I. Enantioselective Acylation of Silyl Ketene Acetals through Fluoride Anion-Binding Catalysis. II. Development of a Practical Method for the Synthesis of Highly Enantioenriched trans-1,2-Amino Alcohols [D] . Birrell, James Andrew 2013

机译：I.通过氟阴离子结合催化对甲硅烷基乙缩醛的对映选择性酰化。二。合成高对映体反式1,2-氨基醇的实用方法的开发
6. New phosphine-diamine and phosphine-amino-alcohol tridentate ligands for ruthenium catalysed enantioselective hydrogenation of ketones and a concise lactone synthesis enabled by asymmetric reduction of cyano-ketones [O] . José A Fuentes, Scott D Phillips, Matthew L Clarke 2012

机译：用于钌催化酮的对映选择性氢化的新膦二胺和膦氨基氨基醇三齿配体以及通过不对称还原氰基酮实现的简洁内酯合成
7. Highly Enantioselective Phase-Transfer-Catalyzed Alkylation of Protected a-Amino Acid Amides toward Practical Asymmetric Synthesis of Vicinal Diamines, a-Amino Ketones, and a-Amino Alcohols [O] . -1

机译：高度映选择性相转移催化的保护A-氨基酸酰胺掺入实际不对称的邻亚胺，A-氨基酮和A-氨基醇的实际不对称合成

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

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