Designing new routes to pharmaceutical reagents via the acid-base reaction of copper(I) oxide with a weak acid in the presence of copper(I) oxide with a weak acid in the presence of a ligand
Charles H. Womack, Megan E. Hinrichsen and Tyler C. Thompson
University of West Florida Libraries
Summer Undergraduate Research Program (University of West Florida, Pensacola, Florida, 2021)
Tris(triphenylphosphine) copper(I) phenolate, (Ph₃P)₃CuOPh, is a possible intermediate in the synthesis of tris(triphenylphosphine) (trifluoromethyl) copper(I), (Ph₃P)₃CuCF₃, which is an
important compound in medicinal chemistry. (Ph₃P)₃CuOPh is synthesized by reacting a copper-containing base (copper(I) oxide, Cu₂O) with a weak acid (phenol, PhOH) in the presence of a ligand (triphenylphosphine, PPh₃). We have been altering the conditions of the acid-base reaction to make our phenolate complex in a timelier and more cost-efficient manner, in high purity. So far, we have experimented with sulfuric, hydrobromic and hydrochloric acids as catalysts in our reactions. Currently, we have lowered the synthesis time to 8 hours from 72 hours and have obtained (Ph₃P)₃CuOPh in acceptable purity with an average of 98% yield. We have also attempted to synthesize a very similar nitromethanide complex, which would serve the same purposes as the phenolate, i.e., as an intermediate in the synthesis of our target compound, (Ph₃P)₃CuCF₃. The current yield is around 80%, and we are trying to improve the purity of this intermediate produced by our method.
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Title
Designing new routes to pharmaceutical reagents via the acid-base reaction of copper(I) oxide with a weak acid in the presence of copper(I) oxide with a weak acid in the presence of a ligand
Resource Type
Poster
Event
Summer Undergraduate Research Program (University of West Florida, Pensacola, Florida, 2021)
Contributors
Dr. A. Timothy Royappa (Faculty Mentor)
Publisher
University of West Florida Libraries; Argo Scholar Commons
Format
1 file; .pdf
Copyright
Permission granted to the University of West Florida Libraries to digitize and/or display this item for non-profit research and educational purposes. Any reuse of this item in excess of fair use or other copyright exemptions requires the permission of the copyright holder.
Identifiers
99380090783706600
Academic Unit
Summer Undergraduate Research Program 2021
Language
English
Designing new routes to pharmaceutical reagents via...