Synthesis of Azidoacetic Acid in Non-Aqueous Solvents
This example provides a general synthetic scheme for
the synthesis of various azidoalkyl acid linkers. To exemplify this
method, the synthesis of 2-azidoacetic acid is provided. Through the
substitution of 2-bromoacetic acid, used in the synthesis of
2-azidoacetic acid, with other reagents azidoalkyl acid linkers, such
as, but not limited to, 3-azidopropionic acid and 2-azoidopropionic
acid, may be produced.
To a solution of 2-bromoacetic acid (1 g, 7.20 mmol) in DMF (14.39 ml) was added sodium azide (0.491 g, 7.56 mmol). After stirring for 16 hours at room temperature, the reaction mixture was monitored by RP HPLC (98% conversion).
H1 NMR analysis (10 mg/mL in CDCl3) showed the relevant peak at 3.84 ppm (s, 2H, N3CH2CO2H).
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To a solution of 2-bromoacetic acid (1 g, 7.20 mmol) in DMF (14.39 ml) was added sodium azide (0.491 g, 7.56 mmol). After stirring for 16 hours at room temperature, the reaction mixture was monitored by RP HPLC (98% conversion).
H1 NMR analysis (10 mg/mL in CDCl3) showed the relevant peak at 3.84 ppm (s, 2H, N3CH2CO2H).
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