1205676-33-0Relevant articles and documents
Process characterization of a monoamine oxidase
Ramesh, Hemalata,Woodley, John M.
, p. 124 - 131 (2014)
Redox biocatalysis is currently gaining focus because it offers exquisite selectivity using mild oxidants, such as oxygen (which is environmentally benign). However, it is often challenging to implement oxidative reactions at scale due to the low activity and stability of the biocatalyst under industrial conditions. Consequently, it becomes critical to identify the bottlenecks for specific oxidation reactions as a first step in scale-up. Subsequently, we can identify where research the effort is required when developing a biocatalytic reaction for implementation in an industrial reaction, i.e., on biocatalyst development (e.g. improvement of expression levels), process development (e.g. improved oxygen supply, product removal strategies) or biocatalyst stabilization (e.g. through immobilization or directed evolution). This paper presents a systematic method to identify the bottleneck of a potential biocatalytic process using a monoamine oxidase to synthesize an intermediate in the manufacture of a drug for treating Hepatitis C (Telaprevir).
Organocatalytic Asymmetric Conjugate Additions to Cyclopent-1-enecarbaldehyde: A Critical Assessment of Organocatalytic Approaches towards the Telaprevir Bicyclic Core
Bernardi, Luca,Fochi, Mariafrancesca,Carbone, Riccardo,Martinelli, Ada,Fox, Martin E.,Cobley, Christopher J.,Kandagatla, Bhaskar,Oruganti, Srinivas,Dahanukar, Vilas H.,Carlone, Armando
, p. 19208 - 19222 (2015)
In the context of a programme directed at the manufacture of telaprevir, eight possible approaches to its bicyclic α-amino acid core, based on organocatalytic enantioselective conjugate additions to cyclopent-1-enecarbaldehyde, were identified and preliminarily explored. Four reactions, delivering advanced intermediates en route to the target amino acid, were selected for a thorough optimisation. Three of this reactions involved iminium ion catalysis with a prolinol catalyst (addition of nitromethane, nitroacetate and acetamidomalonate) and one was based on a Cinchona-derived phase-transfer catalyst (addition of glycine imines). A careful choice of additives allowed lowering of the catalyst loading to 0.5 mol % in some cases. The preparation of intermediates that would give access to the core of telaprevir in good yields and enantioselectivities by exploiting readily available substrates and catalysts, highlights the potential of organocatalytic technology for a cost-effective preparation of pharmaceuticals.
α,α′-C-H Bond Difunctionalization of Unprotected Alicyclic Amines
Valles, Daniel A.,Dutta, Subhradeep,Paul, Anirudra,Abboud, Khalil A.,Ghiviriga, Ion,Seidel, Daniel
supporting information, p. 6367 - 6371 (2021/08/18)
A simple one-pot procedure enables the sequential, regioselective, and diastereoselective introduction of the same or two different substituents to the α- and α′-positions of unprotected azacycles. Aryl, alkyl, and alkenyl substituents are introduced via their corresponding organolithium compounds. The scope of this transformation includes pyrrolidines, piperidines, azepanes, and piperazines.
Intermediate of telaprevir and preparation method thereof
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, (2018/03/26)
The invention discloses an intermediate of telaprevir and a preparation method thereof. The invention specifically discloses a method for preparing a compound shown in the formula 6. The method comprises that a compound shown in the formula 7 or 5 undergoes a reaction under the action of an acid aqueous solution at a temperature of 50-100 DEG C. The preparation method is easy to operate, realizesa low cost, has a high yield, produces a product with high purity and is easy to industrialize.
