Methanol → HCID 59756060, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of compound M (45.4 g, 202 mmol) in 1,4-dioxane (420 mL) was added MeOH (40.9 mL, 1010 mmol) and triethylamine (56.3 mL, 404 mmol). The mixture was heated at 100° C. and diphenylphosphonic azide (65.3 mL, 303 mmol) was dropped into the mixture over 15 minutes. The mixture was stirred at 100° C. for 1 hour and concentrated. The residue was diluted with saturated aqueous NaHCO3 and extracted with ethyl acetate 3 times. The combined organic layers were washed with saturated brine and dried over anhydrous Na2SO4. The combined organic layers were then filtered and evaporated. The resulting residue was crystallized from iPrOH to give a white solid. The solid was dissolved in ethyl acetate and the resulting solution was washed with water and saturated brine and dried over anhydrous Na2SO4. Filtration and evaporation of the solvent gave compound N (33.0 g). In addition, the mother liquid was diluted with ethyl acetate and washed with water and saturated brine, dried over anhydrous Na2SO4, filtered, and evaporated. The resulting residue was recrysatallized from iPrOH to give compound N (4.29 g, 73% total yield) as a white powder. 1H NMR (CDCl3, 400 MHz): δ 2.45 (3H, s), 3.77 (3H, s), 3.84 (3H, s), 3.90 (3H, s), 6.45 (1H, d, J=2.4 Hz), 7.84 (1H, d, J=2.4 Hz), 9.97 (1H, s). EIMS (+): 253 [M]+

Provenance & Evidence