Potassium Carbonate → HCID 462652, compound

Participants

Reaction Steps

To a stirred solution of 52 mg (0.152 mmol) of the (silyloxy)amide 19 in 1.0 mL of acetonitrile, previously cooled in an ice-water bath, was added 500 μL of a 1:3 solution of 30% aqueous hydrofluoric acid solution in acetonitrile. The resulting solution was stirred for 15 minutes in the ice bath, after which time TLC analysis showed the reaction to be complete. The acid was neutralized by cautious addition of about 15 mL of a 10% aqueous potassium carbonate solution to the reaction mixture. The reaction mixture was partitioned between 20 mL of water and 40 mL of ethyl acetate. The layers were separated and the aqueous phase was extracted with 40 mL of ethyl acetate. The combined organic phases were washed with two 50-mL portions of saturated aqueous sodium chloride, dried (Na2SO4) and concentrated in vacuo. The residue (33 mg) was chromatographed over 20 g of silica gel (ethyl acetate) to give 24 mg (71%) of acetamide 20 as an orange oil. 1H NMR (CDCl3) δ6.792 (m, 2H, C=CH; minor isomer), 6.309 (d, J=6.4 Hz, 1H, C=CH; major isomer), 6.269 (d, J=5.6 Hz, 1H, C=CH; major isomer), 6.82 (br s, 1H, NH), 4.276 (br s, 2H, CH2O; minor isomer), 4.512 (d, J=5.6 Hz, 2H, CH2N; minor isomer), 4.228 (br s, 2H, CH2 0; major isomer), 4.023 (d, J=6.0 Hz, 2H, CH2N; major isomer), 2.05 (s, 1H, OH), 1.998 (s, 3H, COCH3 ; major isomer); 13C NMR (CDCl3) δ170.116, 144.100 (minor isomer), 141.214 (minor isomer), 134.827 (major isomer), 132.384 (major isomer), 126.528 (major isomer), 125.815 (minor isomer), 125.254 (minor isomer), 125.178 (major isomer), 64.499 (major isomer), 60.099 (minor isomer), 43.690 (major isomer), 38.631 (minor isomer), 23.140 (major isomer), 21.011 (minor isomer); MS (LSIMS) m/z=57 (100%), 217 (M+).

Provenance & Evidence