5-Azidopentanoic acid

Yellow liquid

5-Azidopentanoic acid can be used to synthesize:

• Chitosan-poly(ethylene glycol) hydrogels by azide–alkyne click chemistry.
• 5-iodo-1,2,3-triazole containing macrocycles.
• Bivalent quinine dimers intervening triazole ring used as inhibitors of P-glycoprotein (P-gp) mediated cellular efflux.

C7H13N302 C5H9N302 29.1 mmol Lithium hydroxide monohydrate as a 1 M solution in Water, 90 ml THF and 90 ml methanol was added to 15.4 mmol Ethyl-5-Azido pentanoate in a flask and stirred at room temperature for 18 hours. The solvent was removed in vacuo and a small amount of water and HCI 37 % was added till pH 1 . After that the reaction mixture was extracted with Ethyl acetate (250 ml) and the combined organic phase was dried over Na2SO4. The solvent was removed in vacuo leaving 2.18 g of 5-Azidopentanoic acid (15.2 mmol, yield = 99 %).^[1]

[1] Duval, S. , &  Kindermann, M. . Azido alkanoic acids and derivatives thereof in feed for reducing methane formation emanating from the digestive activities of ruminants. WO, WO/2011/045418.