Michael J. Di Maso

Impact of Carbon-Based Anode Materials on Selectivity in a Shono Oxidation and Scale Up to Deca-Kilogram Scale

Dan Lehnherr, Longrui Chen, Fazel Bateni, Brandon Pilovsky et autres

We report the development of a selective and scalable Shono oxidation process of Boc- l -proline methyl ester (Boc- l -Pro-OMe) using flow electrosynthesis. A key feature of the reaction is the preferential methoxylation of Boc- l -Pro-OMe at its C5 carbon …

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Development and simulation of annular flow photoreactors: integration of light-diffusing fibers as optical diffusers with laser diodes

Sergio Carrillo De Hert, Rafael Lopez-Rodriguez, Michael J. Di Maso, Jonathan P. McMullen et autres

Laser driven platform for photochemical reactions. Modelling: predictability and optimization.

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Continuous-Flow Solid-Phase Peptide Synthesis to Enable Rapid, Multigram Deliveries of Peptides

Kyle E. Ruhl, Michael J. Di Maso, Harrison B. Rose, Danielle M. Schultz et autres

Peptides may revolutionize the treatment of disease by combining the pharmacological benefits found in both large and small molecules into once-daily oral formulations. For decades, batch-mode solid-phase peptide synthesis (SPPS) has been employed throughout peptide drug discovery and development; however, numerous drawbacks …

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Desymmetrization of Cyclic Sulfonimidamides by Asymmetric Allylation

David A. Gutierrez, Garrett Toth-Williams, Croix J. Laconsay, Michael Yasuda et autres

Herein we report the first transition metal-catalyzed approach to the enantioenriched synthesis of cyclic sulfonimidamides relying on commercially available palladium catalysts and ligands. High-throughput experimentation (HTE) was employed to identify the optimal catalyst system and solvent. The method is applied to a …

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Desymmetrization of Cyclic Sulfonimidamides by Asymmetric Allylation

David A. Gutierrez, Garrett Toth-Williams, Croix J. Laconsay, Michael Yasuda et autres

Abstract Herein we report the first transition metal‐catalyzed approach to the enantioenriched synthesis of cyclic sulfonimidamides relying on commercially available palladium catalysts and ligands. High‐throughput experimentation (HTE) was employed to identify the optimal catalyst system and solvent. The method is applied to …

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Dynamic sampling in autonomous process optimization

Melodie Christensen, Yuting Xu, Eugene E. Kwan, Michael J. Di Maso et autres

Autonomous process optimization (APO) is a technology that has recently found utility in a multitude of process optimization challenges. In contrast to most APO examples in microflow reactor systems, we recently presented a system capable of optimization in high-throughput batch reactor systems. …

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Use of a Dynamic Flow Platform To Translate a Batch Immobilized Transaminase Process to a Packed Bed Reactor for the Synthesis of an Intermediate of Nemtabrutinib

Michael J. Di Maso, Jeffrey T. Kuethe, Karthik Narsimhan, Matthew Burris et autres

Herein we describe the translation of an immobilized transaminase process in batch to a packed bed reactor for the synthesis of cyrene amine, an intermediate of Nemtabrutinib. This change in reactor design provided significant benefits in both robustness of the immobilized enzyme …

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Desymmetrization of Heterocyclic Sulfonimidamides via Asymmetric Tsuji-Trost Asymmetric Alkylation

David Gutierrez, Garrett Toth-Williams, Michael Yasuda, Michael J. Di Maso et autres

Methodologies enabling the synthesis of enantioenriched sulfonimidamides containing a stereogenic sulfur center are scarce, often relying on diastereomeric crystallization or the use of chiral auxiliaries. The prototropic tautomerization exhibited by sulfonimidamides makes them uniquely suited for resolution processes. In the case where …

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CCDC 2267665: Experimental Crystal Structure Determination

David A. Gutierrez, Garrett Toth-Williams, Michael Yasuda, James C. Fettinger et autres

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, …

CCDC 2267666: Experimental Crystal Structure Determination

David A. Gutierrez, Garrett Toth-Williams, Michael Yasuda, James C. Fettinger et autres

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, …

Amination of a Green Solvent via Immobilized Biocatalysis for the Synthesis of Nemtabrutinib

Christopher K. Prier, Karla Camacho Soto, Jacob H. Forstater, Nadine Kuhl et autres

High Resolution Image Download MS PowerPoint Slide Enzymes are capable of unique and selective transformations that can enable efficient chemical production. While many industrial processes have been developed using free enzymes in aqueous solutions, immobilizing enzymes on a solid support can offer …

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Amination of a Green Solvent via Immobilized Biocatalysis for the Synthesis of Nemtabrutinib

Christopher K. Prier, Karla Camacho Soto, Jacob H. Forstater, Nadine Kuhl et autres

Enzymes are capable of unique and selective transformations that can enable sustainable chemical production. While many industrial processes have been developed using free enzymes in aqueous solutions, immobilizing enzymes on a solid support can offer considerable advantages, including improved reaction efficiency, enzyme …

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