Potassium Carbonate → HCID 87726341, compound

Participants

Reaction Steps

To a stirred solution of 3α-(2-trifluoroacetamidoethylthio)-6-(E)-hydroxyiminoandrostan-17-one (Prepn. 78, 115 mg) in MeOH/H2O 95/5 (7 mL), K2CO3 (159 mg) was added. The mixture was refluxed for 1.5 hrs and then concentrated, washed with water, extracted with CH2Cl2 and dried with Na2SO4. Fumaric acid (27 mg) was added and the resulting solution evaporated to dryness. The residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH/NH3 9/1/0.1). To the concentrated fractions a stoichiometric amount of fumaric acid in MeOH was added. The solution was concentrated and the resulting mixture centrifugated. The solid was washed with Et2O/EtOH 9/1 (0.8 mL) to give, after centrifugation, the title compound I-dv (53 mg, 50%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 10.45 (1H, s), 8.10 (3H, m), 6.35 (2H, s), 3.29 (1H, dd), 3.22 (1H, m), 2.86 (2H, t), 2.67 (1H, m), 2.60 (2H, t), 2.50-0.80 (20H, m), 0.76 (3H, s), 0.67 (3H, s).

Provenance & Evidence