Mark T. Barrila
Pfizer
7 Papers
93 Citations
Mark T. Barrila is an academic researcher from Pfizer. The author has contributed to research in topics: Enantioselective synthesis & Hemiaminal. The author has an hindex of 6, co-authored 7 publications.
Chat about Author
Papers
Regio- and Enantioselective Synthesis of Azole Hemiaminal Esters by Lewis Base Catalyzed Dynamic Kinetic Resolution
David W. Piotrowski,Adam S. Kamlet,Anne-Marie R. Dechert-Schmitt,Jiangli Yan,Thomas A. Brandt,Jun Xiao,Liuqing Wei,Mark T. Barrila +7 more
TL;DR: A modular three-component dynamic kinetic resolution that affords enantiomerically enriched hemiaminal esters derived from azoles and aldehydes is reported, which was performed on a multikilogram scale to produce a tetrazole prodrug fragment for a leading clinical candidate that posed formidable synthesis challenges.
59
Regio- and Enantioselective Synthesis of Azole Hemiaminal Esters by Lewis Base Catalyzed Dynamic Kinetic Resolution.
David W. Piotrowski,Adam S. Kamlet,Anne-Marie R. Dechert-Schmitt,Jiangli Yan,Thomas A. Brandt,Jun Xiao,Liuqing Wei,Mark T. Barrila +7 more
TL;DR: In this paper, a modular three-component dynamic kinetic resolution (DKR) was proposed to obtain enantiomerically enriched hemiaminal esters derived from azoles and aldehydes.
32
A Scalable Route for the Regio- and Enantioselective Preparation of a Tetrazole Prodrug: Application to the Multi-Gram-Scale Synthesis of a PCSK9 Inhibitor
Anne Akin,Mark T. Barrila,Thomas A. Brandt,Anne-Marie R. Dechert-Schmitt,Pascal Dube,David D. Ford,Adam S. Kamlet,Chris Limberakis,Andrew Pearsall,David W. Piotrowski,Brian Quinn,Sarah Rothstein,Jerry S. Salan,Liuqing Wei,Jun Xiao +14 more
TL;DR: In this paper, the synthesis of multigram quantities of small molecule PCSK9 inhibitor (R,S)-3 is described using a safe, multikilogram method to prepare 5-(4-iodo-1-methyl-1H-pyrazol-5-yl)-2H-tetrazole (10).
21
Utilization of ReactIR in Fit for Purpose Process Enablement
TL;DR: In this paper, an efficient four-step synthesis of 1 was described in which utilization of ReactIR was key to efficient processing and reaction monitoring, and key chemical steps included nucleophilic aromatic substitution, iron reduction of aromatic nitro group to aniline, decarboxylation, and ester formation.
21
Use of DOE for Rapid Development of a Red-Al Reduction Process for the Synthesis of 3,4-Isopropylidenedioxypyrrolidine Hydrotosylate
TL;DR: In this article, a statistical design of experiments (DOEDOE) was used to rapidly optimize Red-Al reduction of an imide to produce, after deprotection and salt formation, 3,4-isopropylidenedioxypyrrolidine hydrotosylate (1), an intermediate in the synthesis of Ingliforib.
19