2-Naphthalenesulfonyl chloride → HCID 11798431, compound

Participants

Reaction Conditions

Reaction Steps

Compound (49) (0.056 g, 0.2 mmol) and triethylamine (0.14 mL, 1 mmol) were added sequentially to a solution of 2-naphthalene sulfonyl chloride (0.136 g, 0.6 mmol) in CH2Cl2 (5 mL) at 25° C. The mixture was stirred at 25° C. for 12 h then was concentrated under reduced pressure. Purification of the residue by flash column chromatography (gradient elution 0 to 30% EtOAc in hexanes) provided the title compound (0.09 g, 92.5%): TLC (Rf =0.50; 40% EtOAc/Hexanes); 1H NMR (CDCl3) δ 8.35 (s, 1H), 7.98 (m, 3H) 7.73 (m, 5H), 6.43 (d, 2H, J=8.7), 3.86 (d, 2H, J=9.2), 3.78 (s, 1H), 3.60 (m, 1H), 2.60 (t, 2H, J=10.5), 2.11 (d, 2H, J=13.4), 1.60 (m, 2H), 1.54 (s, 9H); 13C NMR (CDCl3) δ 165.9, 149.9, 135.0, 133.2, 132.2, 131.4, 129.3, 129.2, 129.0, 128.9, 128.0, 127.7, 123.0, 121.1, 111.9, 79.9, 49.0, 45.2, 31.7, 28.4; HRMS (FAB) m/z 467.2019 (M+H)+ (C26H30N2O4S requires 467.2005).

Provenance & Evidence