45 research outputs found
N-Acetylation of Amines in Continuous-Flow with Acetonitrile-No Need for Hazardous and Toxic Carboxylic Acid Derivatives
A continuous-flow acetylation reaction was developed, applying cheap and safe reagent, acetonitrile as acetylation agent and alumina as catalyst. The method developed utilizes milder reagent than those used conventionally. The reaction was tested on various aromatic and aliphatic amines with good conversion. The catalyst showed excellent reusability and a scale-up was also carried out. Furthermore, a drug substance (paracetamol) was also synthesized with good conversion and yield
Homochirality of beta-peptides: a significant biomimetic property of unnatural systems
Homochirality, an interesting phenomenon of life, is mainly an unresolved problem and was thought to be a property of living matter. Herein, we show that artificial beta-peptides have the tendency toward homochiral diastereoselective chain elongation. Chain-length-dependent stereochemical discrimination was investigated in the synthesis of foldamers with various side chains and secondary structures. It was found that there is a strong tendency toward the synthesis of homochiral oligomers. The size of the side chain drastically influenced the selectivity of the stereodiscriminative chain-elongation reaction. It is noteworthy that water as the co-solvent increases the selectivity. Such behavior is a novel fundamental biomimetic property of foldamers with a potential of future industrial application
N-Acetylation of Amines in Continuous-Flow with Acetonitrile—No Need for Hazardous and Toxic Carboxylic Acid Derivatives
A continuous-flow acetylation reaction was developed, applying cheap and safe reagent, acetonitrile as acetylation agent and alumina as catalyst. The method developed utilizes milder reagent than those used conventionally. The reaction was tested on various aromatic and aliphatic amines with good conversion. The catalyst showed excellent reusability and a scale-up was also carried out. Furthermore, a drug substance (paracetamol) was also synthesized with good conversion and yield
Accelerated Synthesis of Protected Peptides in a Continuous-Flow Fixed-Bed Reactor
Continuous flow technologies are of considerable current interest. These methods offer several advantages over conventional batch procedures, such as faster heat and mass transfer, shorter reaction time, etc. Herein we show the development of a continuous procedure for the solid-phase synthesis of protected peptide sequences. Importantly, the synthesis of peptides is more than twice as fast as methods in the published literature. Nonetheless, the protected sequences are constructed in a highly sustainable way, because solvent usage is an order of magnitude lower than those in known literature technologies. The developed method has shown excellent sidechain protecting group tolerance with a wide range of chemical functionalities. The efficacy of the technology is demonstrated by the synthesis of various calcitonin and corticotropin fragments. Importantly, the products formed with excellent conversion and were isolated in high purity
Strategic application of residence time control in continuous flow reactors
As a sustainable alternative for conventional batch-based synthetic techniques, the concept of continuous-flow processing has emerged in the synthesis of fine chemicals. Systematic tuning of the residence time, a key parameter of continuous-reaction technology, can govern the outcome of a chemical reaction by determining the reaction rate and the conversion and by influencing the product selectivity. This review furnishes a brief insight into flow reactions in which high chemo- and/or stereoselectivity can be attained by strategic residence-time control and illustrates the importance of the residence time as a crucial parameter in sustainable method development. Such a fine reaction control cannot be performed in conventional batch reaction set-ups