Experimental
Lab Synthesis:
54 mg of compound 18 and 60mg of N-Bocguanidine was added to 1.05 mL of THF and heated to 55O C for 24 hours. This solvent was removed under reduced pressure and flash chromatography was used to separate the compound to yield compound SI-8 contaminated with compound 22 and residual N-Bocguanidine. To finish creating compound 19, 34 mg of the product (from the above reaction) was put in 1.0 mL of dichloromethane. 169 mg of Di-tert-butyl dicarbonate, 105 mg triethylamine, and 1 crystal of dimethylaminopyridine was added to the solution and stirred for 3 hours. This solvent was removed under reduced pressure and purified by PTLC to yield compound 19 as a colorless oil. The total yield for this reaction is 33%.
Compounds in Reaction:
THF is tetrahydrofuran which is a very polar ether. It has a low freezing point which makes good to use in a variety of temperatures. It is used as the solvent in this reaction.
Boc is another name for Di-tert-butyl dicarbonate. Boc is used as a proctecting group on amines so that further reactions will not affect the amine groups. These Boc groups can later be removed using different acids to return to the amine functional group.
Triethylamine (TEA) is a commonly used base that usually acts in elimination reactions. In this reaction however, TEA was used in order to make the solution more basic so that the Boc group could attach to the nitrogens quicker and using less energy.
Dimethylaminopyridine (DMAP) is used as a catalyst in many reactions involving esters and anhydrides. In this reaction, the catalyst was used to help the reaction move faster to the product of compound 19.
Bocguanidine was used as the reactant that replaced the carbonyl group of compound 18.