Green Synthesis of d,l-Phenylalanine using 2-Methylhydrofuron

Abstract: Green Synthesis of d,l-Phenylalanine using 2-Methyltetrahdrofuron

Johnay Fanning, Nicole Blanshan, Rachel Scherrer

Phenylalanine is an amino acid with many uses. The two forms, d, and l interact differently with chiral enzymes. The d form is found in compounds such as aspirin and salicylic acid, and is used to combat pain. The l form is used as a stimulant, appetite suppressant, and mood enhancer. Interestingly, the two forms together are used by the brain to produce norepinephrine, an important neurotransmitter. It also helps to replace dopamine. This three step synthesis started with the saponification of diethyl benzylmalonate to create benzylmalonic acid. This was then converted to bromobenzylmalonic acid via an S_N2 reaction. This second step was also attempted using a greener solvent by changing from diethyl ether to 2-methyltetrahydrofuron. Finally, the bromobenzylmalonic acid was decarboxylated to produce the final product phenylalanine.