Ammonium Chloride → HCID 178452178, compound

Participants

Reaction Steps

To a solution of Example 30A (300 mg, 0.67 mmol) in anhydrous DMF (4 mL) was added sodium azide (522 mg, 8.04 mmol) followed by ammonium chloride (428.8 mg, 8.04 mmol). The mixture was flushed with nitrogen, then exposed to microwave irradiation (20 W, 175° C.) for 15 minutes. The mixture was concentrated under reduced pressure to afford a brown oil. The brown oil was purified by RP-HPLC to provide the titled compound. MS (ESI) m/e 488 (M+H)+, 486 (M−H)−; 1H NMR (300 MHz, CD3OD) δ ppm 1.39 (s, 6 H) 1.47 (s, 3 H) 1.68 (m, 1 H) 1.94 (m, 1 H) 2.59 (m, 2 H) 3.02 (m, 1 H) 3.14 (m, 1 H) 3.23 (m, 1 H) 3.48 (m, 2 H) 3.79 (m, 2 H) 4.56 (m, 2 H) 4.72 (m, 1 H) 7.55 (t, 1 H) 7.82 (d, 1 H) 8.18 (dd, 1 H) 8.44 (s, 1 H).

Provenance & Evidence