1H-1,2,3-Triazole-1-acetic acid, 4-[[bis[[1-(1,1-diMethylethyl)-1H-1,2,3-triazol-4-yl]Methyl]aMino]Methyl]-

18523-48-3

1257633-68-3

1334179-85-9

To a 20 mL screw cap vial equipped with a stirrer was added N,N-bis((1-(tert-butyl)-1H-1,2,3-triazol-4-yl)methyl)prop-2-yn-1-amine (109 mg, 0.33 mmol, 1.0 eq.) and azidoacetic acid (50 mg, 0.50 mmol, 1.5 eq.) in 3 mL tetrahydrofuran (THF). N,N'-diisopropylethylamine (68 mg, 0.53 mmol, 1.6 equiv) and tris(triphenylphosphine)copper(I) bromide (31 mg, 0.033 mmol, 10 mol%) were subsequently added to the mixture. The reaction mixture was sealed and stirred vigorously at 60°C overnight. Upon completion of the reaction, 2 mL of water and about 0.2 g of CupriSorb were added to the mixture and stirring was continued for 30 minutes before filtration. The filtrate was concentrated under reduced pressure and the resulting crude product was purified by fast column chromatography (25 g silica gel, eluent 40% methanol/ethyl acetate solution containing 1% acetic acid, Rf = 0.2, KMnO4 color development) to give 109 mg of the target product (76% yield) as a white solid.1H NMR (300 MHz, D2O) δ 8.22 (s, 2H), 8.14 (s 1H), 5.10 (s, 2H), 4.72 (s, 2H), 4.39 (s, 4H), 1.66 (s, 18H).