Scaling Production of L-Vinyglycine
Mentor 1
Dr. Alan Schwabacher
Location
Union Wisconsin Room
Start Date
24-4-2015 2:30 PM
End Date
24-4-2015 3:45 PM
Description
L-Vinylglycine is a non-protein amino acid which has several properties that make it valuable. While L-Vinylglycine had been successfully synthesized by our group an easier, larger scale production method was desired. / / The scaled production of L-Vinylglycine was developed through experimentation regarding several key factors. The synthesis was carried out under varying conditions regarding the initial mixture of reagents, the temperature at which the primary reaction occurs, the receiving solution or lack thereof, and the retrieval of product from final reaction mixture. The synthesis was carried out using a basic distillation apparatus under a nitrogen atmosphere. / / The rate of addition of the initial reaction mixture appears to have the largest effect on the overall yield when using this method of synthesis. The rate of hydrolysis of the silyl protecting groups on the L-Vinylglycine was dramatically increased by the presence of ethanol in the receiving flask of the basic distillation apparatus used in the synthesis. Initial findings suggest the temperature at which the elimination of the sulfenic acid occurs appears to have little effect on the purity of the product when using this method. / / The success of the synthesis was primarily assessed through the yield of the product and the purity according its NMR spectra. A standard set of reaction conditions was developed, giving relatively pure L-Vinylglycine at an acceptable yield. This method could be used to easily and rapidly produce large quantities of L-Vinylglycine for further research. / /
Scaling Production of L-Vinyglycine
Union Wisconsin Room
L-Vinylglycine is a non-protein amino acid which has several properties that make it valuable. While L-Vinylglycine had been successfully synthesized by our group an easier, larger scale production method was desired. / / The scaled production of L-Vinylglycine was developed through experimentation regarding several key factors. The synthesis was carried out under varying conditions regarding the initial mixture of reagents, the temperature at which the primary reaction occurs, the receiving solution or lack thereof, and the retrieval of product from final reaction mixture. The synthesis was carried out using a basic distillation apparatus under a nitrogen atmosphere. / / The rate of addition of the initial reaction mixture appears to have the largest effect on the overall yield when using this method of synthesis. The rate of hydrolysis of the silyl protecting groups on the L-Vinylglycine was dramatically increased by the presence of ethanol in the receiving flask of the basic distillation apparatus used in the synthesis. Initial findings suggest the temperature at which the elimination of the sulfenic acid occurs appears to have little effect on the purity of the product when using this method. / / The success of the synthesis was primarily assessed through the yield of the product and the purity according its NMR spectra. A standard set of reaction conditions was developed, giving relatively pure L-Vinylglycine at an acceptable yield. This method could be used to easily and rapidly produce large quantities of L-Vinylglycine for further research. / /
