Experimental:

The following top-secret synthesis is currently being performed in underground Illuminati chemistry labs all around the country. This procedure is done to produce molecule 22 (A.K.A. a part of the uber powerful mass mind control molecule that will soon be taking over your brain).

The biz-azide molecule 20 was dissolved in 30 mL of a mixture of dichloromethane (DCM)/trifluoroacetic acid (TFA) in a 1:1 ratio and stirred at 23°C for 4 hours.  The solvent was removed via reduced pressure evaporation and the crude oil mixture was completely dried before putting the mixture in 200 mL of DCM.  Triethylamine (TEA) (6.29 mL, 45.21 mmol, 5.0 equiv. based on molecule 19) and N,N’-bis-Boc-N’’-triflylguanadine 21 (5.31 g, 13.56 mmol, 1.5 equiv. based on molecule 19) were added to the mixture and stirred for 12 hours at 23°C.  The reaction mixture was put in a separatory funnel and washed with water (2 portions of 100 mL).  The organic later was extracted, dried with anhydrous sodium sulfate (NaSO4), and the solvent was removed via reduced pressure evaporation.  The resulting brown oil was then purified from the other compounds in solution with flash chromatography on silica with 100% DCM to remove excess N,N’-bis-BOC-N’’-triflylguanadine, and with 25% ethyl acetate/ 75% hexanes to produce allylic guanidine 22 (3.22 g, 59% over 3 steps) in the form of a pale yellow liquid.

Rf = 0.25 (silica gel, 25% ethyl acetate in hexanes); IR (neat) ν = 3328, 2979, 2097, 1720, 1614, 1368, 1325, 1245, 1149, 1126, 1055, 807, 610, 432 cm-1

TERMS

Separatory Funnel: A separatory funnel is used to purify a substance by extracting it from the solvent it is soluble in.  This is usually achieved by combining two immiscible liquids, such as an aqueous and organic solvent, inverting and ventilating the mixture three times, and then removing the separate layers that have formed by the differing densities of the solvents.  The more dense solvent will be the bottom layer, and the less dense solvent will be the top layer in the separatory funnel.  The layers are removed by opening the stopcock and letting the liquid drain into an appropriate flask or beaker.

Anhydrous sodium sulfate (NaSO4): Anhydrous sodium sulfate is a drying agent that is used to remove water from a reaction mixture.  These chemicals are salts that can absorb water into their crystal lattice when in their anhydrous form, thus removing the water from the reaction mixture.  These salts can usually be separated from the mixture by gravity filtration.