Potassium Carbonate → 11-Azidoundecanoic acid

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Sodium azide (2.38 gr, 44.3 mmol) was dissolved in 7.5 mL of water and added to a round bottom flask containing 15 mL of dichloromethane. The flask was cooled to 0° C. and trifluoromethanesulfonic anhydride (1.5 mL, 8.9 mmol) was added dropwise. The resulting solution was allowed to warm to room temperature and was stirred for two hours. The aqueous layer was extracted with dichloromethane (3×8 mL), and the combined organic phases were washed with a saturated solution of sodium carbonate. The resulting solution was then slowly added to a suspension of 11-aminoundecanoic acid (892 mg, 4.43 mmol), K2CO3 (915 mg, 6.62 mmol), and CuSO4.5H2O (11 mg, 0.0044 mmol) in 15 mL of water and 22.5 mL of methanol. The mixture was stirred overnight, and concentrated in vacuo. The solution was acidified with 1 M HCl solution and extracted with dichloromethane (4×50 mL). The organic phases where combined, dried with magnesium sulfate, filtered and concentrated in vacuo, yielding 5c at 92%. 1H-NMR (200 MHz, CDCl3): 1.25-1.4 (m; 12H), 1.5-1.7 (m; 4H), 2.35 (t; J=7.43 Hz; 2H), 3.25 (t; J=6.88 Hz; 2H).

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