Work

Synthesis of (S)-3-Amino-4-(difluoromethylenyl)-cyclopent-1-ene-1-carboxylic Acid (OV329), a Potent Inactivator of γ-Aminobutyric Acid Aminotransferase

Year: 2018

Type: article

Abstract: ( S)-3-Amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid (OV329, 1) is being developed for the treatment of epilepsy and addiction. The previous 14-step synthesis of OV329 was low yielding, involved an unselective α-elimination to form the cyclopentene, required the use of tert-butyllithium, and produced toxic selenium byproducts in the penultimate step. A new synthesis, which avoids the aforementioned issues, was carried out on large scale, reducing the step count from 14 to 9 steps and increasing the overall yield from 3.7% to 8.1%.

Source: Organic Letters

DOI: 10.1021/acs.orglett.8b01872

Authors: Matthew J. Moschitto, Richard B. Silverman

Institutions: Northwestern University, Chemistry of Life Processes Institute

Language: English

Topic: Fluorine in Organic Chemistry

Subfield: Pharmaceutical Science

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

SDG: Good health and well-being

Open Access status: green

Funders: Styrelsen för Internationellt Utvecklingssamarbete, National Institutes of Health, International Institute for Nanotechnology, Northwestern University, National Institute on Drug Abuse