A GLC and GC/MS study of the reaction between benzylpenicillin and BF3-methanol

A study of the reaction of BF3-methanol with benzylpenicillin showed that penicillin could be converted to a form suitable for gas-liquid chromatography. This study indicated possible use of the reaction in an analytical method for penicillin, by determining the methyl phenylacetate product. A reaction rate and yield study was conducted using gas-liquid chromatography employing an internal standard for improved measurement accuracy. The reaction gave a relatively constant yield of 70 +/- 2% and was complete in less than 1 minute. Investigations of the identity of side products were conducted using GC/MS, UV, and IR. A variety of products, including penicillenates, penillates, penilloates, and acrylic acid esters, were indicated at very mild reaction conditions.