SU278031A1 - METHOD OF OBTAINING SODIUM SALT 6- - Google Patents
METHOD OF OBTAINING SODIUM SALT 6-Info
- Publication number
- SU278031A1 SU278031A1 SU1266419A SU1266419A SU278031A1 SU 278031 A1 SU278031 A1 SU 278031A1 SU 1266419 A SU1266419 A SU 1266419A SU 1266419 A SU1266419 A SU 1266419A SU 278031 A1 SU278031 A1 SU 278031A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- sodium salt
- obtaining sodium
- acid
- butyl acetate
- mol
- Prior art date
Links
- 159000000000 sodium salts Chemical class 0.000 title 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- UWYHMGVUTGAWSP-JKIFEVAISA-N Oxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1 UWYHMGVUTGAWSP-JKIFEVAISA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229960001019 oxacillin Drugs 0.000 description 3
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-APA Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PENHKTNQUJMHIR-UHFFFAOYSA-N 5-methyl-3-phenyl-1,2-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=C(C)ON=C1C1=CC=CC=C1 PENHKTNQUJMHIR-UHFFFAOYSA-N 0.000 description 1
- 229940064005 Antibiotic throat preparations Drugs 0.000 description 1
- 229940083879 Antibiotics FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE Drugs 0.000 description 1
- 229940042052 Antibiotics for systemic use Drugs 0.000 description 1
- 229940042786 Antitubercular Antibiotics Drugs 0.000 description 1
- 229940093922 Gynecological Antibiotics Drugs 0.000 description 1
- 229940024982 Topical Antifungal Antibiotics Drugs 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000003115 biocidal Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229940079866 intestinal antibiotics Drugs 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940005935 ophthalmologic Antibiotics Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Description
Изобретение относитс к фармакологии, а именно к методам получени антибиотиков .The invention relates to pharmacology, in particular to methods for producing antibiotics.
В основном авт. св. № 343978 описан способ получени оксациллина, согласно которому взаимодействию подвергают 6-аминопенициллановую кислоту и хлорангидрид 3-фенил5-метилизоксазол-4-карбоновой кислоты в водно-ацетановой среде в присутствии бикарбоната натри с последующей экстракцией полученного продукта бутилацетатом и обработкой натриевой солью уксусной кислоты. Реакцию ведут при комнатной температуре, что приводит к получению продукта 90%-ной степени чистоты.Basically auth. St. № 343978 discloses a process for preparing oxacillin, according to which the interaction is subjected to 6-aminopenicillanic acid chloride and 3-fenil5-methylisoxazole-4-carboxylic acid in atsetanovoy aqueous medium in the presence of sodium bicarbonate, followed by extraction of the resulting product by treatment with sodium acetate and acetic acid salt. The reaction is carried out at room temperature, which results in a product of 90% purity.
Цель изобретени - повышение качества целевого продукта. Дл этого обработку ацетатом натри ведут при температуре около 50°С, что позвол ет повысить чистоту препарата до 95-97%.The purpose of the invention is to improve the quality of the target product. For this, treatment with sodium acetate is carried out at a temperature of about 50 ° C, which makes it possible to increase the purity of the preparation to 95-97%.
Пример. Смесь 0,965 моль 5-метил-Зфенилизоксазол - 4 - карбоновойкислоты,Example. A mixture of 0.965 mol 5-methyl-Zphenylisoxazole - 4 - carboxylic acid,
1,13 моль тионилхлорида и 2 жл диметилформамида в 304 мл бензола перемешивают 3 час при 52--56°С и затем упаривают в вакууме при этой же температуре дл удалени избытка тионилхлорида. Получают 210 г хлорангидрид а 5-метил-3-фенилизоксазол-4карбоновой кислоты (93,6% от теоретического количества).1.13 mol of thionyl chloride and 2 g of dimethylformamide in 304 ml of benzene are stirred for 3 hours at 52--56 ° C and then evaporated in vacuo at the same temperature to remove excess thionyl chloride. 210 g of acid chloride a 5-methyl-3-phenylisoxazole-4carboxylic acid are obtained (93.6% of the theoretical amount).
0,9 моль полученного хлорангидрида без дополпительной очистки раствор ют в 1 л ацетона, и при перемешивании в течение 20 мин добавл ют к охлажденному до О-0.9 mol of the acid chloride obtained without further purification is dissolved in 1 l of acetone, and with stirring for 20 minutes, it is added to the cooled to O-
2°С раствору 0,94 моль 6-аминопенициллановой кислоты и 200 г бикарбоната натри в 5 л воды и 1,4 л ацетона. Смесь перемешивают 2,5 час при комнатной температуре и дважды экстрагируют по I л бутилацетата.2 ° C to a solution of 0.94 mol of 6-aminopenicillanic acid and 200 g of sodium bicarbonate in 5 liters of water and 1.4 liters of acetone. The mixture is stirred for 2.5 hours at room temperature and extracted twice with 1 l of butyl acetate.
Водный слой отдел ют и снова экстрагируют 1,6 л бутилацетата при подкислении до рН 2,35-3,0 10%-ной серной кислотой (0,85 л). Экстракцию при рН 2,35 повтор ют с использованием 1 л бутилацетата. ОбъединенныйThe aqueous layer was separated and extracted again with 1.6 L of butyl acetate, while acidifying to pH 2.35-3.0 with 10% sulfuric acid (0.85 L). The extraction at pH 2.35 is repeated using 1 L of butyl acetate. Combined
бутилацетатный экстракт промывают водой, сушат сульфатом магни , фильтруют, нагревают до 50°С и обрабатывают 5 мин 0,94 люль измельченного ацетата натри . После по влени осадка смесь слабо перемешиваютThe butyl acetate extract is washed with water, dried over magnesium sulfate, filtered, heated to 50 ° C and treated with 0.94% of ground sodium acetate for 5 minutes. After the precipitate appears, the mixture is stirred gently.
2,5 час при постепенном снижении температуры до 30°С. Полученный осадок отдел ют, промывают 1 л бутилацетата и два раза по 1 л ацетона, а затем сушат при 50-60°С и остаточном давлении 5-10 мм рт. ст. в течение 3 час. Получают 317 г оксациллина 97%-ной степени чистоты (74,3% от теоретического количества). 3 лановой кислоты (оксациллина) по основному авт. св. № 343978, отличающийс тем, что, с целью повышени качества целевого продук4 та, обработку ацетатом натр.и ведут при температуре около 50°С. 2.5 hours with a gradual decrease in temperature to 30 ° C. The precipitate obtained is separated, washed with 1 liter of butyl acetate and twice with 1 liter of acetone, and then dried at 50-60 ° C and a residual pressure of 5-10 mm Hg. Art. within 3 hours Obtain 317 g of oxacillin 97% purity (74.3% of theoretical amount). 3 lanoic acid (oxacillin) on the main ed. St. No. 343978, characterized in that, in order to improve the quality of the target product, the treatment with sodium acetate is carried out at a temperature of about 50 ° C.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU278031A1 true SU278031A1 (en) |
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