Molecular Formula | C21H30O3 |
Molar Mass | 330.46 |
Density | 1.11±0.1 g/cm3(Predicted) |
Melting Point | 111-114 °C |
Boling Point | 447.6±45.0 °C(Predicted) |
Use | Triton acetate is a synthetic 19-desandrosterone, has weak estrogenic, androgenic and progestogenic activity, and is useful for the treatment of climacteric syndrome. |
The preparation of triptorone acetate is as follows:
Put tetrahydrofuran (717.6g), compound (5A)(204g) and anhydrous copper acetate (II)(23.6g) into a suitable container. Stir the slurry and cool to between -45°C and -35°C. Then, the methyl magnesium chloride solution (23%, dissolved in THF, analytical concentration is 22.6%,346.1g) is slowly added at a rate of maintaining the reaction temperature between -45°C and -35°C for a minimum period of 3 hours. After the addition was completed, the reaction mixture was stirred between -45°C and -35°C and monitored by HPLC. Then, finish the mixture with 37% hydrochloric acid (128.1g) and keep the temperature below 10 ℃. The mixture was maintained below 10°C for 30 minutes. During about 20 minutes, slowly add water (408g). Add heptane (428.2g) and heat the mixture to room temperature. The aqueous phase layer was separated and the product was extracted with heptane. The combined organic extract was washed with 25% ammonium hydroxide solution and purified water. The solvent was distilled at atmospheric pressure until about 3 volumes [feed volume relative to compound (5A)] were retained. The tert-butyl methyl ether was added and the mixture was cooled to crystallize the product tritorone acetate. The product was separated by filtration and dried at 40-50 ℃ (yield: 78%;α∶β ratio = 99).