Sodium Azide → HCID 19377651, compound

Participants

Reaction Conditions

Reaction Steps

(±)-N-(2,6-diisopropylphenyl)-2-(2-dodecyl -2H-tetrazol-5-yl)-2-bromoacetamide (1 g, 1.87 mmol) from Example 1 (e) was added to a solution containing sodium azide (0.24 g, 3.7 mmol) in ethanol (20 mL). The solution was stirred for 72 hours at 24° C. Sodium borohydride (0.07 g, 1.87 mmol) was added to the reaction mixture in one portion. The suspension was stirred for 12 hours at 24° C., then concentrated in vacuo. The resulting residue was triturated with ethyl acetate, filtered, and the filtrate was concentrated in vacuo leaving a viscous liquid. The liquid was dissolved in 10 mL of 50% ethyl acetate/ 50% hexane and purified by silica gel chromatography (elution with 50% ethyl acetate/50% hexane) to give (±)-2-amino-N-(2,6-diisopropylphenyl)-2-(2-dodecyl -2H-tetrazol-5-yl)-acetamide (0.58 g, 66%) as a colorless liquid;

Provenance & Evidence