Jason M. Stevens

Bristol-Myers Squibb (United States)

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Eric M. Simmons

Bristol-Myers Squibb (United States)

Victor W. Rosso

Bristol-Myers Squibb (United States)

Steven R. Wisniewski

Bristol-Myers Squibb (United States)

Albert J. DelMonte

Bristol-Myers Squibb (United States)

Peng Geng

Xi'an Jiaotong University

Merrill L. Davies

Bristol-Myers Squibb (United States)

Andrew W. Glace

Bristol-Myers Squibb (United States)

Sergei Kolotuchin

Bristol-Myers Squibb (United States)

Neil A. Strotman

Merck & Co., Inc., Rahway, NJ, USA (United States)

Gregory L. Beutner

Bristol-Myers Squibb (United States)

Cooperative Institutions

Bristol-Myers Squibb (United States)

116

The Bristol-Myers Squibb Children's Hospital

Bristol-Myers Squibb (Germany)

Princeton University

Merck & Co., Inc., Rahway, NJ, USA (United States)

Scripps Research Institute

Biocon (India)

Bristol-Myers Squibb (India)

University of Illinois Urbana-Champaign

Pfizer (United States)

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Direct Lewis Acid Catalyzed Conversion of Enantioenriched N-Acyloxazolidinones to Chiral Esters, Amides, and Acids

The Journal of Organic Chemistry (2018)

Jason M. Stevens Ana Cristina Parra-Rivera Darryl D. Dixon Gregory L. Beutner Albert J. DelMonte

The identification of Yb(OTf)3 through a multivariable high-throughput experimentation strategy has enabled a unified protocol for the direct conversion of enantioenriched N-acyloxazolidinones to the corresponding chiral esters, amides, and carboxylic acids. This straightforward and catalytic method has shown remarkable chemoselectivity for substitution at the acyclic N-acyl carbonyl for a diverse array of N-acyloxazolidinone substrates. The ionic radius of the Lewis acid catalyst was demonstrated as a key driver of catalyst performance that led to the identification of a robust and scalable esterification of a pharmaceutical intermediate using catalytic Y(OTf)3.

Chemoselectivity

Lewis acid catalysis

Amide

10.1021/acs.joc.8b02451

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Citations (32)

High-Throughput Automation in Chemical Process Development

Annual Review of Chemical and Biomolecular Engineering (2017)

Joshua A. Selekman Jun Qiu Kristy Tran Jason M. Stevens Victor W. Rosso

High-throughput (HT) techniques built upon laboratory automation technology and coupled to statistical experimental design and parallel experimentation have enabled the acceleration of chemical process development across multiple industries. HT technologies are often applied to interrogate wide, often multidimensional experimental spaces to inform the design and optimization of any number of unit operations that chemical engineers use in process development. In this review, we outline the evolution of HT technology and provide a comprehensive overview of how HT automation is used throughout different industries, with a particular focus on chemical and pharmaceutical process development. In addition, we highlight the common strategies of how HT automation is incorporated into routine development activities to maximize its impact in various academic and industrial settings.

Laboratory automation

Process development

10.1146/annurev-chembioeng-060816-101411

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Citations (108)

Bayesian reaction optimization as a tool for chemical synthesis

Nature (2021)

Benjamin J. Shields Jason M. Stevens Jun Li Marvin Parasram Farhan Damani

Bayesian Optimization

Engineering optimization

Benchmark (surveying)

10.1038/s41586-021-03213-y

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Citations (626)

CCDC 2210685: Experimental Crystal Structure Determination

The Cambridge Structural Database (2022)

Cong Bi James Chadwick Merrill L. Davies Albert J. DelMonte Peng Geng

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, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc2d6dfg

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A Multi-Objective Active Learning Platform and Web App for Reaction Optimization

José Garrido Torres Sii Hong Lau Pranay Anchuri Jason M. Stevens José E. Tábora

We report the development of an open-source Experimental Design via Bayesian Optimization platform for multi-objective reaction optimization. Using high-throughput experimentation (HTE) and virtual screening datasets containing high-dimensional continuous and discrete variables, we optimized the performance of the platform by fine-tuning the algorithm components such as reaction encodings, surrogate model parameters and initialization techniques. Having established the framework, we applied the optimizer to real-word test scenarios for the simultaneous optimization of reaction yield and enantioselectivity in a Ni/photoredox-catalyzed enantioselective cross-electrophile coupling of styrene oxide with two different aryl iodide substrates. Starting with no previous experimental data, the Bayesian optimizer identified reaction conditions that surpassed the previously human-driven optimization campaigns within 15 and 24 experiments, for each substrate, among 1,728 possible configurations available in each optimization. To make the platform more accessible to non-experts, we developed a Graphical User Interface (GUI) that can be accessed online through a web-based application and incorporated features such as conditions modification on-the-fly and data visualization. This web-application does not require software installation, removing any programming barrier to use the platform, which enables chemists to integrate Bayesian optimization routines into their everyday laboratory practices.

Bayesian Optimization

Initialization

10.26434/chemrxiv-2022-cljcp

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Citations (10)

Rapid Development of a Commercial Process for Linrodostat, an Indoleamine 2,3-Dioxygenase (IDO) Inhibitor

Organic Process Research & Development (2019)

Kenneth J. Fraunhoffer Albert J. DelMonte Gregory L. Beutner Michael Bultman Kathryn M. Camacho

The process development and the kilogram-scale synthesis of linrodostat (BMS-986205, 1) are described. The synthesis features several highly efficient telescoped processes and the use of Evans auxiliary to install a methyl-bearing stereocenter. The target was prepared in 12 steps with 7 isolations in an overall yield of 31%.

Indoleamine 2,3-dioxygenase

Stereocenter

Process development

10.1021/acs.oprd.9b00359

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Citations (26)

CCDC 2210683: Experimental Crystal Structure Determination

The Cambridge Structural Database (2022)

Cong Bi James Chadwick Merrill L. Davies Albert J. DelMonte Peng Geng

10.5517/ccdc.csd.cc2d6dcd

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Advances in Base-Metal Catalysis: Development of a Screening Platform for Nickel-Catalyzed Borylations of Aryl (Pseudo)halides with B₂(OH)₄

Organometallics (2018)

John R. Coombs Rebecca A. Green F. E. ROBERTS Eric M. Simmons Jason M. Stevens

Investigations into nickel-catalyzed borylation reactions have led to the development of an experimental design of 24 reaction conditions for rapid lead identification. A case study on the borylation of a model aryl bromide with B2(OH)4 prompted a series of mechanistic and stability studies to better understand the catalytic cycle and factors that affect robustness. HTEx was employed to study the effect of a series of scavengers on the remediation of nickel from the reaction stream. These combined results have generated an increased understanding of nickel-catalyzed borylation reactions and set the stage for their expanded use in process chemistry.

Borylation

Catalytic cycle

10.1021/acs.organomet.8b00307

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Citations (32)

High-Throughput Salt Screening of Synthetic Intermediates: Effects of Solvents, Counterions, and Counterion Solubility

Organic Process Research & Development (2020)

Jun Qiu Anisha Patel Jason M. Stevens

Using a statistical Z-score methodology, the yield data from 65 high-throughput acid screens and 45 base screens on synthetic intermediates were analyzed. The results show that salt screening outcomes are largely determined by the choice of counterions and solvents. We rank-ordered counterions, solvents, and counterion/solvent combinations and provided recommendations on how to carry out more productive high-throughput salt screening on synthetic intermediates.

High-Throughput Screening

10.1021/acs.oprd.0c00132

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Citations (21)

Synthesis and SAR of vinca alkaloid analogues

Bioorganic & Medicinal Chemistry Letters (2008)

Matthew E. Voss Jeffery M. Ralph Dejian Xie David D. Manning Xinchao Chen

Vinca

HeLa

Vinca alkaloid

10.1016/j.bmcl.2008.12.077

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Citations (25)