tert-Butanol → HCID 25234712, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product from Example 26 (75 mg, 0.146 mmol) in tert-butanol (4 ml) was added diphenylphosphoryl azide (47 μL 0.219 mmol) and triethylamine (31 μL, 0.219 mmol). The resulting mixture was stirred at 80° C. for 18 h. The cooled mixture was partitioned between H2O (10 ml) and EtOAc (2×10 ml). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using 3% MeOH in CH2Cl2 as the eluent to give the title compound (16 mg, 19%). 1H NMR (300 MHz, DMSO-d6) δ 11.45 (d, J=1.84 Hz, 1 H) 9.86 (s, 1 H) 9.03 (s, 1 H) 7.75 (d, J=7.72 Hz, 2 H) 7.55 (d, J=2.57 Hz, 1 H) 7.10-7.33 (m, 4 H) 7.04 (dd, J=8.64, 2.39 Hz, 1 H) 5.66 (dd, J=7.91, 2.02 Hz, 1 H) 3.78 (s, 3 H) 3.02 (s, 3 H) 1.45 (s, 9 H) 1.38 (s, 9 H).

Provenance & Evidence