SU371217A1 - WAY OF OBTAINING 3,16-DIACETATE PREGNEN-5-TRIOL-Zr, 16a, 17a-SHE-20 - Google Patents
WAY OF OBTAINING 3,16-DIACETATE PREGNEN-5-TRIOL-Zr, 16a, 17a-SHE-20Info
- Publication number
- SU371217A1 SU371217A1 SU1670464A SU1670464A SU371217A1 SU 371217 A1 SU371217 A1 SU 371217A1 SU 1670464 A SU1670464 A SU 1670464A SU 1670464 A SU1670464 A SU 1670464A SU 371217 A1 SU371217 A1 SU 371217A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- diacetate
- pregnen
- triol
- obtaining
- way
- Prior art date
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
1one
Изобретение относитс к способам получени производных р да прегнена, вл ющихс промежуточными продуктами в синтезе высокоактивных препаратов.The invention relates to methods for producing derivatives of the series of pregnanes, which are intermediate products in the synthesis of highly active drugs.
Р1звестны способы получени 3,16-диацетата прегнен-5-триол-Зр, 6а, 17а-она-20 кип чением 3,17-диацетата-16р-бромпрегнен-5-диол-Зр , 17а-она-20 с одним из следующих агентов: ацетатом натри в уксусной кислоте (выход ) ацетатом серебра (выход ---97%), пиридином в этиловом спирте (выход ), коллидином (выход 69%). Эти методы или дают относительно низкий выход целевого продукта или же, как в случае с ацетатом серебра, требуют применени труднодоступного и дорогосто щего реагента.Methods for obtaining 3,16-diacetate of pregnen-5-triol-3p, 6a, 17a-one-20 are known by boiling 3,17-diacetate-16p-bromopregnen-5-diol-3p, 17a-one-20 with one of the following agents: sodium acetate in acetic acid (yield) silver acetate (yield --- 97%), pyridine in ethyl alcohol (yield), collidine (yield 69%). These methods either give a relatively low yield of the target product or, as is the case with silver acetate, require the use of an inaccessible and expensive reagent.
С целью повышени выхода и упрощени технологии процесса в качестве органического азотистого основани используют анилин в эквимолекул рном отношении к стероиду. При этом выход целевого продукта становитс количественным . Кроме того, анилин вл етс легкодоступным и дешевым реагентом.In order to increase the yield and simplify the process technology, aniline is used as an organic nitrogenous base in an equimolar ratio to the steroid. At the same time, the yield of the target product becomes quantitative. In addition, aniline is an easily available and inexpensive reagent.
Способ получени 3,16-диацетата прегнен-5-триол-Зр , 16а, 17а-она-20 заключаетс в том, что 3,17-диацетат-16р-бром-прегнен-5-диол-Зр, 17а-она-20 кип т т с эквимолекул рным количеством анилина в пол рных растворител х, например спирте, и целевой продукт выдел ЕОт известными приемами.The method for preparing 3,16-diacetate pregnen-5-triol-3p, 16a, 17a-one-20 is that 3,17-diacetate-16p-bromo-pregnen-5-diol-3p, 17a-one-20 boil with an equimolar amount of aniline in polar solvents, such as alcohol, and the target product is isolated with EO by known techniques.
Пример. Раствор 1 г 3,17-диацетат-16р-бромпрегнен-З-диол-Зр , 17а-она-20 и 0,188 г анилцна в 20 мл спирта кип т т при перемешивании с обратным холодильником 5 час. Затем из реакционной массы отгон ют в вакууме спирт, остаток размешивают с водой, осадок отфильтровывают, промывают водой, сушат Н получают 0,83 г (95%) 3,16-диацетата прегнен-5-триол-Зр, 16а, 17а-она-20, т. пл. 204-206°С (из абсолютного спирта), а о -°- 70,8° (с 1,0: СНСЬ).Example. A solution of 1 g of 3.17-diacetate-16p-bromopregnen-3-diol-3p, 17a-one-20, and 0.188 g of anilce in 20 ml of alcohol is boiled under reflux with stirring for 5 hours. Then from the reaction mass, the alcohol is distilled off in vacuum, the residue is stirred with water, the precipitate is filtered off, washed with water, dried, H is obtained 0.83 g (95%) of 3.16-diacetate of pregnen-5-triol-3p, 16a, 17a-she -20, so pl. 204-206 ° С (from absolute alcohol), and о - ° - 70.8 ° (с 1.0: СНСЬ).
ИК-спектр, V слг-: 3530(ОН), 1725 (СО- сложнозфирна ), 1705 (СО - карбонил).IR spectrum, V slg-: 3530 (OH), 1725 (CO-complex), 1705 (CO-carbonyl).
ПМР-спектр 18-СНз-б 0,73 м. д. (синглет); 19-СНз-б 1,01 м. д. (синглет); 3-ОАс, 16-ОАс, 17-Ас-б 2,03-2,26 м. д. (три синглета); 3-Н-б 4, 5 м.д. (мультиплет); 6-Н-б 5,76 м. д. (мультиплет ); 16-Н-б 5,36 м. д. (мультиплет).H-spectrum of 18-CH3-b 0.73 ppm (singlet); 19-CH3-B 1.01 ppm (singlet); 3-OAc, 16-OAc, 17-Ac-b 2.03-2.26 ppm (three singlet); 3-Н-б 4, 5 ppm (multiplet); 6-Н-б 5.76 ppm (multiplet); 16-Nb 5.36 ppm (multiplet).
Найдено, %: С 69,27; Н 8,30.Found,%: C 69.27; H 8.30.
С25НзбОб.С25Нббобоб.
Вычислено, %: С 69,42; Н 8,39.Calculated,%: C 69.42; H 8.39.
Предмет изобретени Subject invention
Способ получени 3,16-диацетата прегнен-3-триол-Зр , 16а, 17а-она-20 действием на 3,17- ,а.иацет ат-16р-бромпрегнен-5-диол-Зр, 17а-она-20 органическим азотистым основанием при кип чении R пол рных растворител х с выделением целевого продукта известными приемаа ми, отличающийс тем, что, с целью повышеНИН выхода и упрощени технологии процесса, в качестве органического азотистого основа4 ни используют эквимолекул рное количество анилина. The method of obtaining 3,16-diacetate of pregnen-3-triol-3p, 16a, 17a-one-20 by action of 3.17-, a.i acetat-16p-bromopregnen-5-diol-3p, 17a-she-20 organic a nitrogenous base at the boiling point of R polar solvents with isolation of the target product by known methods, characterized in that, in order to increase the yield and simplify the process technology, an equimolar molecular amount of aniline is used as the organic nitrogenous base4.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1670464A SU371217A1 (en) | 1971-06-21 | 1971-06-21 | WAY OF OBTAINING 3,16-DIACETATE PREGNEN-5-TRIOL-Zr, 16a, 17a-SHE-20 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1670464A SU371217A1 (en) | 1971-06-21 | 1971-06-21 | WAY OF OBTAINING 3,16-DIACETATE PREGNEN-5-TRIOL-Zr, 16a, 17a-SHE-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU371217A1 true SU371217A1 (en) | 1973-02-22 |
Family
ID=20479405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1670464A SU371217A1 (en) | 1971-06-21 | 1971-06-21 | WAY OF OBTAINING 3,16-DIACETATE PREGNEN-5-TRIOL-Zr, 16a, 17a-SHE-20 |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU371217A1 (en) |
-
1971
- 1971-06-21 SU SU1670464A patent/SU371217A1/en active
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