Experimental:
Compound 24 (2.38 g, 4.32 mmol, 1.0 equiv) was dissolved in a 1:1 mixture of water and TFA (30 mL). After the mixture was stirred 70°C for 36 h, the solvent was evaporated under reduced pressures to form intermediate 6, which did not need further purification. Intermediate 6 was dissolved in acetic acid (10mL) and concentrated. This process was repeated five times to form bis-AcOH salt. The bis-AcOH salt, cyanamide (6.0 g), and saturated NaCl (120mL) were placed into a reaction vessel. The mixture was sonicated for one minute and the pH was adjusted to 5.5 by carefully adding 0.2 M NaOH to reach the pH level. The reaction mixture was refluxed at 70°C for 4h, cooled to room temperature, and concentrated. Then, acetonitrile was added and the NaCl slurry was filtered using vacuum filtration. The compound was purified using high performance liquid chromatography (5% to 40% acetonitrile in water, 0.1% TFA), forming compound 25 (1.91 g, 75% over two steps). The final product, compound 25, was analyzed.

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Glossary:

Sonication: Sonication is the act of applying sound or energy to agitate particles in a compound sample. It can be used to help speed up and mix reactions. In this experiemnt, sonication was used to used to help mix reactants together.

Reflux: A reflux is the process of boiling reactants while continually cooling the vapor and returning it back to the flask as a liquid. The purpose of this method is to maintain a constant temperature without evaporating the reactants and products. This essentially allows for a reaction to occur at high temperatures. In this experiment, reflux was used to allow for the reaction to occur at 70°C.

High performance liquid chromatography (HPLC):HPLC is a technique used to separate and purify components in a mixture. It is a form of column chromatography that pumps a sample of the reaction mixture in a solvent at high pressures through a column. In this experiment, HPLC was used to separate and purify the final compound 25.