Sodium Azide → tert-butyl (4-((3R,4S,5S)-4-azido-3-((tert-butoxycarbonyl)amino)-5-methylpiperidin-1-yl)pyridin-3-yl)(tert-butoxycarbonyl)carbamate

Beteiligte Stoffe

Reaktionsschritte

To a solution of (3R,4R,5S)-1-(3-(bis(tert-butoxycarbonyl)amino)pyridin-4-yl)-3-((tert-butoxycarbonyl)amino)-5-methylpiperidin-4-yl methanesulfonate (1.0 equiv.) in DMF (0.13 M) was added NaN3 (5.0 equiv.). The solution was submerged in an 80° C. oil bath and left stirring under Ar for 24 hrs. The solution was cooled to rt and left stirring under Ar overnight. The solution was partitioned between EtOAc and H2O. The organic layer was washed with Na2CO3(sat), NaCl(sat), dried over MgSO4, filtered, concentrated to yield tert-butyl (4-((3R,4S,5S)-4-azido-3-((tert-butoxycarbonyl)amino)-5-methylpiperidin-1-yl)pyridin-3-yl)(tert-butoxycarbonyl)carbamate in 60% yield. LC/MS (m/z)=548.4 (MH+), Rt=0.94 min. 1H NMR (400 MHz, <cdcl3>) δ ppm 0.97-1.13 (m, 3 H), 1.33-1.52 (m, 30 H), 2.03-2.19 (m, 1 H), 2.66-2.87 (m, 2 H), 3.16 (dd, J=12.72, 2.15 Hz, 1 H), 3.22-3.32 (m, 1 H), 3.81-4.01 (m, 2 H), 4.78 (d, J=9.00 Hz, 1 H), 6.76-6.88 (m, 1 H), 8.05-8.18 (m, 1 H), 8.26-8.37 (m, 1 H).

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