<i>Vibrio cholerae</i>, the causative agent of two of the seven recorded cholera pandemics, is a facultative anaerobic, gram negative bacteria. The main pathogenic effect is life-threatening acute diarrhea that cannot be helped by rehydration or electrolyte therapy. The most common treatment of cholera, like many other bacteria, is through the administration of antibiotics. <i>Vibrio Cholerae</i>, like many bacteria, is developing a resistance to classic antibiotic treatments, which is why the innovation of new treatments is necessary. Virstatin is a compound that takes a new route to treating V. cholerae by inhibiting ToxT, a transcription regulator. The synthesis of virstatin is completed in two steps. The first step of the reaction is a Gabriel synthesis that uses DMF as its solvent. Dimethyl formamide (DMF) is a toxic solvent that does not have any known replacements in reactions like the one being performed. The goal of the current experiment is to green the synthesis of virstatin by discovering a satisfactory benign alternative solvent to DMF. To do so three solvents will be tested for applicability: DMC, CPME, and ethanol. Purity of product, percent yield, and reflux time were taken into account to determine the applicability of each solvent. The purity of the product was determined by NMR, IR, and melting point. TLC was used to monitor the reaction with 1:1 ethyl acetate: hexane as the mobile phase.

Greening the synthesis of virstatin: Finding an alternative solvent to dimethyl formamide

253rd National Meeting (2017)

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