Preparation method of 2,6-dibromo 17a-hydroxyprogesterone
A technology of hydroxyprogesterone and bromine, which is used in the preparation of 1,6-didehydro-17a-hydroxyprogesterone, and in the field of key intermediates in the synthesis of progestogen drug cyproterone acetate, can solve the problem of unsolved problems. DDQ dehydrogenation agent and other problems, to achieve the effect of high product yield, conducive to industrial production, and simple process operation
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[0025] B. Preparation of debrominated compounds
[0026] Dissolve the above bis-bromide in an organic solvent, add lithium chloride and lithium carbonate, heat up to 40-80°C and stir to dissolve, then keep warm at 40-120°C for 2-6 hours, TLC confirms the reaction end point, after the reaction, Adjust the pH to neutral, concentrate under reduced pressure to recover the organic solvent, then cool; add tap water, stir and crystallize at 5-25°C for 3-6 hours, centrifuge, wash, and dry to obtain the debrominated product: 1,6-didehydro- 17a-hydroxyprogesterone crude product, HLPC content 97.0-98.5%, weight yield 62.5.-65.0%.
[0027] C. Crude refined
[0028] Decolorize and recrystallize the above crude debrominated product with activated carbon in low-carbon alcohols below C4 to obtain 1,6-didehydro-17a-hydroxyprogesterone product, with HPLC content of 99.0-99.5%, melting point of 228-232°C, this step The weight yield of the synthesis reaction is 50-55%.
[0029] The specific co...
Embodiment 1
[0037] The preparation of step A, two bromines
[0038] In a 2000ml three-necked flask, add 100g 17a hydroxyprogesterone, 200ml dioxane, 80g 25% hydrobromic acid acetic acid solution, stir to make the system strongly acidic, control the temperature at 25-30°C, and slowly add 140g The solution made of bromine and 600ml dioxane should be dripped within about 1.0-1.5 hours. After the dripping, continue to keep warm at 25-30°C for 4-6 hours. TLC confirms the reaction end point. After the reaction, slowly Slowly add 200ml of 30% hydrosulfite aqueous solution to completely destroy bromine, then concentrate under reduced pressure to recover 90-95% of dioxane, after concentration, cool down to 10-15°C, add 600ml of tap water, stir and crystallize Centrifuge for 3-4 hours, wash with water until neutral, and dry under vacuum below 40°C to obtain 144.8g of bisbromide 2,6-dibromo-17a-hydroxyprogesterone, HLPC content 98.2%, moisture content 3.5%, weight yield 144.8%;
[0039] Step B, sy...
Embodiment 2
[0044] The preparation of step A, two bromines
[0045] In a 2000ml three-necked flask, add 100g 17a hydroxyprogesterone, 500ml toluene, 80g 25% hydrobromic acid aqueous solution, stir to make the system strongly acidic, control the temperature at 25-30°C, slowly add 140g bromine and 300ml The solution made of DMF will be dropped within about 1.0-1.5 hours. After the drop, continue to keep warm at 25-30°C for 4-6 hours. TLC will confirm the reaction end point. After the reaction, slowly add 200ml of 30% Sodium hydrosulfite aqueous solution to completely destroy bromine, then wash twice with 600ml tap water, separate the water, dry with 50g anhydrous magnesium sulfate, and concentrate under reduced pressure to recover 90-95% of the mixed solvent of toluene and DMF. After concentration, Cool down to 10-15°C, add 600ml of tap water, stir and crystallize for 3-4 hours, centrifuge, wash with water until neutral, and dry in vacuum below 40°C to obtain the dibromo 2,6-dibromo-17a-hyd...
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