4-Azidobenzenesulfonamide → (2S,3S)-ethyl-3-((S)-1-oxo-1-((1-(4-sulfamoylphenyl)-1H-1,2,3-triazol-4-yl)methylamino)-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate

Participants

Reaction Steps

The general click procedure was used substituting the following quantities using: 37 (109.0 mg, 0.31 mmol): 4-azidobenzenesulfonamide (61.5 mg, 0.31 mmol); CuSO4 (10.0 mg, 0.06 mmol); NaAsc (20.0 mg, 0.03 mmol); TBTA (10.0 mg, 0.02 mmol); in t-BuOH/EtOH/H2O (4:4:2); afforded the 42 as a white solid (119 mg, 69.8%). 1H NMR (CDCl3, 400 MHz): δ 8.93 (s, 1H); 8.45 (s, 1H); 8.39-8.05 (q, 4H); 7.33 (s, 1H); 4.83-4.77 (t, 1H); 4.57-4.48 (q, 2H); 4.28-4.23 (q, 2H); 3.64 (s, 1H); 3.50 (s, 1H); 3.40-3.21 (m, 2H); 1.28-1.23 (t, 3H). 13C NMR (MeOD-d4, 100 MHz): 170.94, 166.80, 166.72, 153.45, 151.92, 145.70, 143.49, 138.85, 127.31, 120.74, 139.76, 115.56, 61.42, 52.72, 52.67, 51, 47, 33.93, 31.91, 12.52.

Provenance & Evidence