ERIC Number: EJ1458743
Record Type: Journal
Publication Date: 2024-Feb
Pages: 9
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: EISSN-1938-1328
An Expedient Undergraduate Synthesis of Glycerol Phenylbutyrate, One of the Most Expensive Medications in the United States
Marquis T. Yazzie; Max E. Wilkins; Brianna N. Marez; Shannon M. Killian; Jacob J. Mitchell; Fatima Chavez-Esparza; Kevin Lopez; Kateri A. Ahrendt
Journal of Chemical Education, v101 n2 p578-586 2024
The urea cycle disorder drug glycerol phenylbutyrate (Ravicti) is presently one of the most expensive medications in the United States, with annual costs estimated at $800,000 as of 2023. An expedient synthesis of this orphan drug was successfully adapted for the undergraduate organic chemistry laboratory. Activation of 4-phenylbutyric acid with thionyl chloride cleanly affords 4-phenylbutyryl chloride, which is then esterified with glycerol in the presence of N-methylimidazole. Glycerol phenylbutyrate is obtained in high yield and purity following silica gel column chromatography. It is anticipated that this synthesis can be readily implemented in other undergraduate organic chemistry laboratory programs, fostering student interest and engagement by highlighting the relevance of chemistry to the societal issue of drug pricing.
Descriptors: Undergraduate Study, College Science, Science Education, Scientific Concepts, Medicine, Organic Chemistry, Science Laboratories
Division of Chemical Education, Inc. and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Research
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A