Methyl p-toluenesulfonate → HCID 86621632, compound

Participants

Reaction Steps

Compound C4 (1.92 g, 5.73 mmol) was suspended in DMF (10 mL), methyl-p-toluenesulfonate (15 mL) was added, and the mixture was stirred at room temperature for 18 h. Solvent was removed under reduced pressure and the residue was dissolved in warm MeOH (10 mL), then diluted with EtOAc. Some of the MeOH was boiled off, and the solution was then refrigerated for 18 h. The resulting precipitate was filtered, and washed with EtOAc to give essentially pure C5 (2.90 g, 97%), which was used without further purification. 1H NMR [(CD3)2SO] δ10.85 (s, 1 H, CONH), 10.60 (s, 1 H, NH), 8.33-8.27 (m, 4 H, H-3′,5′ & py H-2,6), 8.08-8.30 (m, 2 H, H-2′,6′), 7.94-7.89 (m, 2 H, H-2″ 4″), 7.69 (t, J=7.9 Hz, 1 H, H-5″), 7.60-7.57 (m, 1 H, H-6″), 7.48-7.45 (m, 2 H, H-3, 5), 7.22 (d, J=7.5 Hz, 2 H, p-tol H-2,6), 7.20 (d, J=8.1 Hz, 2 H, p-tol H-3,5), 3.99 (s, 3 H, N+CH3), 1.99 (s, 3 H, CH3).

Provenance & Evidence