HCID 10316106, compound → HCID 9837054, compound

Participants

Reaction Steps

Compound 12 (1 g, 2.8 mmol) was dissolved in CF3CO2H (20 mL) which had been precooled in an ice bath. This mixture was stirred overnight at room temperature. The acid was removed under vacuum and the residue dried under high vacuum overnight. This residue was dissolved in water (1 mL) and subjected to cation-exchange chromatography (AG 50W-X8, column volume=3 mL). The column was eluted with water, and the fractions corresponding to product were evaporated to dryness. The residue was dissolved in a small amount of water and lyophilized to give 0.33 g (59%) of 3 as a white solid: mp 190°-194° C. dec; [α]D +2.5° (c 0.28, H2O); 1H NMR (300 MHz, D2O) δ 2.9 (s, 3 H, CH3), 2.96-3.0 (m, 2 H, CH2), 3.97 (dd, J=6.41 and 7.02 Hz 1 H α-CH ) 6.6 (m, 1 H, C=CH ); 13C NMR (75 MHz, D2O) δ 23.53 (CH3), 26.57 (CH2), 52.96 (α-C), 130.07 (C=C), 143.79 (C=C), 172.59 (C=O), 172.72 (C=O), 173.01 (C=O). FAB-MS m/z 199 (MH)+. Anal. (C8H10N2O4.1/3H2O) C, H, N.

Provenance & Evidence