Lawesson's reagent → HCID 86590643, compound

Participants

Reaction Steps

Lawesson's reagent (119 mg, 0.29 mmol) was added under argon to a solution of 15 (0.167 g, 4.19 mmol) in anhydrous 1,2-dichloroethane (11 mL) and the reaction mixture was stirred overnight under reflux. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography [eluent: stepwise gradient of methanol (1–2%) in chloroform] to give pure 16 (0.165 g, 95%) as a yellow foam. 1H-NMR (DMSO-d6): δ 12.81 (s, 1H, NH), 7.64 (s, 1H, H-6), 5.84 (d, 1H, H-1′, J1′-2′=4.66 Hz), 5.5–5.4 (m, 2H, H-2′ and H-3′), 4.11 (dd, 2H, H-5′ and H-5″, J=11.7 Hz, J=31.3 Hz), 2.0–1.8 (m, 12H, 3 CH3CO2 and CH3), 1.33 (s, 3H, CH3); MS (matrix GT): FAB>0 m/z 829 (2M+H)+, 415 (M+H)+, 273 (S)+, 143 (BH2)+, 43 (CH3CO)+ FAB<0 m/z 827 (2M−H)−, 413 (M−H)−, 141 (B)31 , 59 (CH3CO2)−.

Provenance & Evidence