CN112125819B - Preparation method of dencichine - Google Patents
Preparation method of dencichine Download PDFInfo
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- CN112125819B CN112125819B CN202010839809.9A CN202010839809A CN112125819B CN 112125819 B CN112125819 B CN 112125819B CN 202010839809 A CN202010839809 A CN 202010839809A CN 112125819 B CN112125819 B CN 112125819B
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- C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
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Abstract
The invention relates to the field of pharmaceutical chemistry, in particular to a preparation method of dencichine. The preparation method of dencichine provided by the invention comprises the following steps: introducing an organic alcohol solution of Boc-D-2, 3-diaminopropionic acid and an organic alcohol solution of monoethyl oxalate into a microchannel reactor for reaction to obtain a reaction effluent liquid; concentrating the reaction discharging liquid, adding water, and stirring under an acidic condition to obtain a reaction liquid containing dencichine; filtering and washing the reaction solution containing the dencichine to obtain the dencichine. The preparation method of dencichine provided by the invention can prepare dencichine with high yield without adding alkaline substances, has mild reaction conditions and short reaction time, and is beneficial to industrial production.
Description
Technical Field
The invention relates to the field of pharmaceutical chemistry, in particular to a preparation method of dencichine.
Background
Notoginseng radix is also called Notoginseng radix, and the main monomer hemostatic active substance in Notoginseng radix is dencichine. The dencichine is a non-protein free amino acid in pseudo-ginseng, has hemostatic active ingredients, can stop bleeding by increasing the number of platelets in the body and shorten the time of coagulation and bleeding, is widely used for traumatic hemorrhage treatment and the like, and is an active ingredient of various traditional prescriptions such as Yunnan white drug powder and the like.
In the prior art, CN109180532A discloses a preparation method of dencichine, which comprises the following steps: placing 50% methanol aqueous solution and N-alpha-Boc-D-alpha, beta-diaminopropionic acid into a reaction kettle, cooling to 0-5 ℃, adding lithium hydroxide monohydrate in batches, measuring the pH value to about 8, stirring, dissolving potassium monomethyl oxalate in the methanol aqueous solution, dropwise adding into the reaction solution, and keeping the temperature at 0-5 ℃ in the process; after the dripping is finished, the temperature is raised to room temperature for reaction; filtering, washing the filter cake with methanol water solution and acetone for one time, and drying to obtain white solid; adding the solid into water, cooling to below 10deg.C, dropwise adding 2N hydrochloric acid, adjusting pH to 2.1-2.2, and controlling the temperature at 0-10deg.C; after the dripping is completed, stirring for 2-3 hours at room temperature, carrying out suction filtration, and purifying a filter cake to obtain a white solid product. In the preparation method of the dencichine, a large amount of alkaline substances are required to be added and the reaction is carried out under alkaline conditions, however, the addition of the alkaline substances can certainly increase the production cost and the separation difficulty of the later-stage products.
Disclosure of Invention
The invention aims to overcome the defects that the existing method for preparing the dencichine needs to add alkaline substances and is carried out under alkaline conditions, so that the production cost and the product separation difficulty are increased, and further provides a preparation method of the dencichine.
In order to achieve the above purpose, the invention adopts the following technical scheme:
a preparation method of dencichine comprises the following steps:
1) Introducing an organic alcohol solution of Boc-D-2, 3-diaminopropionic acid and an organic alcohol solution of monoethyl oxalate into a microchannel reactor for reaction to obtain a reaction effluent liquid;
2) Concentrating the reaction discharging liquid, adding water, and stirring under an acidic condition to obtain a reaction liquid containing dencichine;
3) Filtering and washing the reaction solution containing the dencichine to obtain the dencichine.
The structure of the dencichine is as follows:
the synthetic route of the dencichine is as follows:
preferably, the reaction temperature in step 1) is 20-30 ℃, the reaction pressure is 0.1-0.3MPa, and the residence time is 30-60min.
Preferably, the flow rate of the organic alcohol solution of Boc-D-2, 3-diaminopropionic acid is 12-14.1g/min, and the flow rate of the organic alcohol solution of monoethyl oxalate is 11-15.4g/min.
Preferably, the preparation method of the organic alcohol solution of Boc-D-2, 3-diaminopropionic acid comprises the steps of mixing Boc-D-2, 3-diaminopropionic acid with an organic alcohol aqueous solution to obtain the organic alcohol solution of Boc-D-2, 3-diaminopropionic acid;
the preparation method of the organic alcohol solution of the monoethyl oxalate comprises the step of mixing the monoethyl oxalate with an organic alcohol aqueous solution to obtain the organic alcohol solution of the monoethyl oxalate.
Preferably, the mass ratio of the Boc-D-2, 3-diaminopropionic acid to the organic alcohol aqueous solution in the organic alcohol solution of the Boc-D-2, 3-diaminopropionic acid is (0.2-0.41) 1; the mass ratio of the oxalic acid monoethyl ester to the organic alcohol aqueous solution in the organic alcohol solution of the oxalic acid monoethyl ester is (0.11-0.29): 1.
Preferably, the organic alcohol aqueous solution is a methanol aqueous solution.
Preferably, the mass fraction of the methanol in the methanol aqueous solution is 30-50%.
Preferably, the molar ratio of Boc-D-2, 3-diaminopropionic acid to monoethyl oxalate is 1: (1-1.2).
Preferably, in the step 2), the reaction effluent is concentrated, the pH of the solution is adjusted to 2.0-3.0 after adding water, and then the reaction solution containing dencichine is obtained after stirring for 4-6 hours under the acidic condition.
Preferably, the solvents used in the washing step are water, methanol and acetone.
The microchannel reactor is an existing device and can be obtained by means of the commercial method and the like.
The invention has the beneficial effects that:
1) According to the preparation method of dencichine, organic alcohol solution of Boc-D-2, 3-diaminopropionic acid and organic alcohol solution of monoethyl oxalate are introduced into a micro-channel reactor for reaction, so that reaction effluent liquid is obtained; concentrating the reaction discharging liquid, adding water, and stirring under an acidic condition to obtain a reaction liquid containing dencichine; filtering and washing the reaction solution containing the dencichine to obtain the dencichine. According to the preparation method, the organic alcohol solution of Boc-D-2, 3-diaminopropionic acid and the organic alcohol solution of monoethyl oxalate are introduced into the microchannel reactor for reaction, and high-yield sanchi can be prepared by utilizing the efficient heat and mass transfer effects of the microchannel reactor without adding alkaline substances, and meanwhile, the preparation method disclosed by the invention is mild in reaction condition and short in reaction time, greatly improves the production efficiency, saves the production cost and is beneficial to industrial production.
2) The preparation method of dencichine provided by the invention further comprises the steps of 1) wherein the reaction temperature is 20-30 ℃, the reaction pressure is 0.1-0.3MPa, and the residence time is 30-60min. The invention can further improve the yield of sanchinin by controlling the reaction temperature, the reaction time and the reaction pressure.
3) According to the preparation method of dencichine, the flow rate of the organic alcohol solution of Boc-D-2, 3-diaminopropionic acid is 12-14.1g/min, and the flow rate of the organic alcohol solution of monoethyl oxalate is 11-15.4g/min. The invention can further improve the yield of sanchinin by matching the conditions.
Detailed Description
The following examples are provided for a better understanding of the present invention and are not limited to the preferred embodiments described herein, but are not intended to limit the scope of the invention, any product which is the same or similar to the present invention, whether in light of the present teachings or in combination with other prior art features, falls within the scope of the present invention.
The specific experimental procedures or conditions are not noted in the examples and may be followed by the operations or conditions of conventional experimental procedures described in the literature in this field. The reagents or apparatus used were conventional reagent products commercially available without the manufacturer's knowledge.
The microchannel reactors used in the following examples and comparative examples of the present invention were purchased from the company of micro-fluidic technologies, inc., of Suzhou, model WH-IND152.
Example 1
The embodiment provides a preparation method of dencichine, which comprises the following steps:
1) Adding Boc-D-2, 3-diaminopropionic acid (204.23 g) into 30% methanol water solution (1000 g) with mass fraction, stirring and mixing to prepare a methanol solution of Boc-D-2, 3-diaminopropionic acid;
adding (118 g) of monoethyl oxalate into 30% methanol aqueous solution (1000 g) with stirring and mixing to prepare methanol solution of monoethyl oxalate;
2) Simultaneously pumping a methanol solution of Boc-D-2, 3-diaminopropionic acid and a methanol solution of monoethyl oxalate into a microchannel reactor by using a metering pump to perform reaction (controlling the flow rate of the methanol solution of Boc-D-2, 3-diaminopropionic acid to be 12.04g/min and the flow rate of the methanol solution of monoethyl oxalate to be 11.18 g/min), wherein the reaction temperature is 20 ℃, the reaction pressure is 0.2MPa, the residence time is 40min, and a reaction effluent liquid is obtained after the reaction is finished;
3) Concentrating the reaction discharge liquid under reduced pressure to obtain a concentrated solution, adding 50ml of water into the concentrated solution, regulating the pH value of the solution to 2.1 by using 0.5mol/L hydrochloric acid, and stirring and reacting for 5 hours at normal temperature to obtain a reaction liquid containing dencichine; cooling the reaction solution containing dencichine to 0 ℃, stirring at 0 ℃ for 2 hours, carrying out suction filtration, adding a filter cake into ice water, stirring for 3 hours, carrying out suction filtration, pulping and washing the filter cake with 50ml ice water, 50ml methanol and 50ml acetone for two times respectively, and drying to obtain the dencichine product with the yield of 94% and the purity of 99.3%.
Example 2
The embodiment provides a preparation method of dencichine, which comprises the following steps:
1) Adding Boc-D-2, 3-diaminopropionic acid (408.46 g) into 50% methanol water solution (1000 g) with mass fraction, stirring and mixing to prepare methanol solution of Boc-D-2, 3-diaminopropionic acid;
adding oxalic acid monoethyl ester (283.4 g) into a 50% methanol aqueous solution (1000 g) by mass fraction, stirring and mixing to prepare a methanol solution of oxalic acid monoethyl ester;
2) Simultaneously pumping a methanol solution of Boc-D-2, 3-diaminopropionic acid and a methanol solution of monoethyl oxalate into a microchannel reactor by using a metering pump to perform reaction (controlling the flow rate of the methanol solution of Boc-D-2, 3-diaminopropionic acid to be 14.08g/min and the flow rate of the methanol solution of monoethyl oxalate to be 15.4 g/min), wherein the reaction temperature is 30 ℃, the reaction pressure is 0.3MPa, the residence time is 30min, and a reaction effluent liquid is obtained after the reaction is finished;
3) Concentrating the reaction discharge liquid under reduced pressure to obtain a concentrated solution, adding 50ml of water into the concentrated solution, regulating the pH value of the solution to 2 by using 0.5mol/L hydrochloric acid, and stirring and reacting for 6 hours at normal temperature to obtain a reaction liquid containing dencichine; cooling the reaction solution containing dencichine to 0 ℃, stirring at 0 ℃ for 2 hours, carrying out suction filtration, adding a filter cake into ice water, stirring for 3 hours, carrying out suction filtration, pulping and washing the filter cake with 50ml ice water, 50ml methanol and 50ml acetone for two times respectively, and drying to obtain the dencichine product with the yield of 92% and the purity of 99.4%.
Example 3
The embodiment provides a preparation method of dencichine, which comprises the following steps:
1) Adding Boc-D-2, 3-diaminopropionic acid (204.23 g) into 30% methanol water solution (1000 g) with mass fraction, stirring and mixing to prepare a methanol solution of Boc-D-2, 3-diaminopropionic acid;
adding (118 g) of monoethyl oxalate into 30% methanol aqueous solution (1000 g) with stirring and mixing to prepare methanol solution of monoethyl oxalate;
2) Simultaneously pumping a methanol solution of Boc-D-2, 3-diaminopropionic acid and a methanol solution of monoethyl oxalate into a microchannel reactor by using a metering pump to perform reaction (controlling the flow rate of the methanol solution of Boc-D-2, 3-diaminopropionic acid to be 12.04g/min and the flow rate of the methanol solution of monoethyl oxalate to be 11.18 g/min), wherein the reaction temperature is 25 ℃, the reaction pressure is 0.1MPa, the residence time is 60min, and a reaction effluent liquid is obtained after the reaction is finished;
3) Concentrating the reaction discharge liquid under reduced pressure to obtain a concentrated solution, adding 50ml of water into the concentrated solution, regulating the pH value of the solution to 3 by using 0.5mol/L hydrochloric acid, and stirring and reacting for 4 hours at normal temperature to obtain a reaction liquid containing dencichine; cooling the reaction solution containing dencichine to 0 ℃, stirring at 0 ℃ for 2 hours, carrying out suction filtration, adding a filter cake into ice water, stirring for 3 hours, carrying out suction filtration, pulping and washing the filter cake with 50ml ice water, 50ml methanol and 50ml acetone for two times respectively, and drying to obtain the dencichine product with the yield of 91% and the purity of 99.6%.
Example 4
The embodiment provides a preparation method of dencichine, which comprises the following steps:
1) Adding Boc-D-2, 3-diaminopropionic acid (204.23 g) into 30% methanol water solution (1000 g) with mass fraction, stirring and mixing to prepare a methanol solution of Boc-D-2, 3-diaminopropionic acid;
adding (118 g) of monoethyl oxalate into 30% methanol aqueous solution (1000 g) with stirring and mixing to prepare methanol solution of monoethyl oxalate;
2) Simultaneously pumping a methanol solution of Boc-D-2, 3-diaminopropionic acid and a methanol solution of monoethyl oxalate into a microchannel reactor by using a metering pump to perform reaction (controlling the flow rate of the methanol solution of Boc-D-2, 3-diaminopropionic acid to be 12.04g/min and the flow rate of the methanol solution of monoethyl oxalate to be 11.18 g/min), wherein the reaction temperature is 26 ℃, the reaction pressure is 0.22MPa, the residence time is 55min, and a reaction effluent liquid is obtained after the reaction is finished;
3) Concentrating the reaction discharge liquid under reduced pressure to obtain a concentrated solution, adding 50ml of water into the concentrated solution, regulating the pH value of the solution to 2.6 by using 0.5mol/L hydrochloric acid, and stirring at normal temperature for reacting for 4.5 hours to obtain a reaction liquid containing dencichine; cooling the reaction solution containing dencichine to 0 ℃, stirring at 0 ℃ for 2 hours, carrying out suction filtration, adding a filter cake into ice water, stirring for 3 hours, carrying out suction filtration, pulping and washing the filter cake with 50ml ice water, 50ml methanol and 50ml acetone for two times respectively, and drying to obtain the dencichine product with the yield of 93% and the purity of 99.4%.
Comparative example 1
The comparative example provides a preparation method of dencichine, which comprises the following steps:
1) Adding Boc-D-2, 3-diaminopropionic acid (204.23 g) into 30% methanol water solution (1000 g) with mass fraction, stirring and mixing to prepare a methanol solution of Boc-D-2, 3-diaminopropionic acid;
adding (118 g) of monoethyl oxalate into 30% methanol aqueous solution (1000 g) with stirring and mixing to prepare methanol solution of monoethyl oxalate;
2) Adding a methanol solution of Boc-D-2, 3-diaminopropionic acid and a methanol solution of monoethyl oxalate into a reaction kettle for reaction, wherein the reaction temperature is 20 ℃, the reaction pressure is 0.2MPa, the reaction time is 20 hours, and a reaction effluent liquid is obtained after the reaction is finished;
3) Concentrating the reaction discharge liquid under reduced pressure to obtain a concentrated solution, adding 50ml of water into the concentrated solution, regulating the pH value of the solution to 2.1 by using 0.5mol/L hydrochloric acid, and stirring and reacting for 5 hours at normal temperature to obtain a reaction liquid containing dencichine; cooling the reaction solution containing dencichine to 0 ℃, stirring at 0 ℃ for 2 hours, carrying out suction filtration, adding a filter cake into ice water, stirring for 3 hours, carrying out suction filtration, pulping and washing the filter cake with 50ml ice water, 50ml methanol and 50ml acetone for two times respectively, and drying to obtain the dencichine product with the yield of 44% and the purity of 88.2%.
It is apparent that the above examples are given by way of illustration only and are not limiting of the embodiments. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary here nor is it exhaustive of all embodiments. While still being apparent from variations or modifications that may be made by those skilled in the art are within the scope of the invention.
Claims (9)
1. The preparation method of the dencichine is characterized by comprising the following steps:
1) Introducing an organic alcohol solution of Boc-D-2, 3-diaminopropionic acid and an organic alcohol solution of monoethyl oxalate into a microchannel reactor for reaction to obtain a reaction effluent liquid;
2) Concentrating the reaction discharging liquid, adding water, and stirring under an acidic condition to obtain a reaction liquid containing dencichine;
3) Filtering and washing a reaction solution containing dencichine to obtain the dencichine;
no alkaline substance is added in the reaction process in the step 1);
the reaction temperature in the step 1) is 20-30 ℃, the reaction pressure is 0.1-0.3MPa, and the residence time is 30-60min.
2. The method for preparing dencichine according to claim 1, wherein the flow rate of the organic alcohol solution of Boc-D-2, 3-diaminopropionic acid is 12-14.1g/min, and the flow rate of the organic alcohol solution of monoethyl oxalate is 11-15.4g/min.
3. The method for preparing dencichine according to claim 1, wherein the method for preparing organic alcohol solution of Boc-D-2, 3-diaminopropionic acid comprises mixing Boc-D-2, 3-diaminopropionic acid with organic alcohol aqueous solution to obtain organic alcohol solution of Boc-D-2, 3-diaminopropionic acid;
the preparation method of the organic alcohol solution of the monoethyl oxalate comprises the step of mixing the monoethyl oxalate with an organic alcohol aqueous solution to obtain the organic alcohol solution of the monoethyl oxalate.
4. The method for preparing dencichine according to claim 3, wherein the mass ratio of Boc-D-2, 3-diaminopropionic acid to organic alcohol aqueous solution in organic alcohol solution of Boc-D-2, 3-diaminopropionic acid is (0.2-0.41): 1; the mass ratio of the oxalic acid monoethyl ester to the organic alcohol aqueous solution in the organic alcohol solution of the oxalic acid monoethyl ester is (0.11-0.29): 1.
5. The method for preparing dencichine according to claim 4, wherein the aqueous solution of organic alcohol is aqueous solution of methanol.
6. The method for preparing dencichine according to claim 5, wherein the mass fraction of methanol in the aqueous methanol solution is 30-50%.
7. The method for preparing dencichine according to claim 1, wherein the molar ratio of Boc-D-2, 3-diaminopropionic acid to monoethyl oxalate is 1: (1-1.2).
8. The process for preparing dencichine according to claim 1, wherein in step 2), the reaction effluent is concentrated, the pH of the solution is adjusted to 2.0-3.0 after adding water, and then the reaction solution containing dencichine is obtained by stirring for 4-6 hours under the acidic condition.
9. The method for preparing dencichine according to claim 1, wherein the solvents used in the washing step are water, methanol and acetone.
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Citations (4)
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|---|---|---|---|---|
| CN1292377A (en) * | 2000-08-10 | 2001-04-25 | 昆明南国生物资源开发研究所 | Synthesis preparation method of high-effective hemostatic notoginseng extract |
| CN105061247A (en) * | 2015-08-19 | 2015-11-18 | 西安岳达植物科技有限公司 | Improved synthesis method for dencichine |
| CN105439883A (en) * | 2015-12-11 | 2016-03-30 | 中国医学科学院药用植物研究所 | Preparation method and application of D-dencichine |
| CN109180532A (en) * | 2018-08-29 | 2019-01-11 | 南京天际联盟医药科技有限公司 | The high efficiency preparation method of D- dencichine |
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2020
- 2020-08-19 CN CN202010839809.9A patent/CN112125819B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1292377A (en) * | 2000-08-10 | 2001-04-25 | 昆明南国生物资源开发研究所 | Synthesis preparation method of high-effective hemostatic notoginseng extract |
| CN105061247A (en) * | 2015-08-19 | 2015-11-18 | 西安岳达植物科技有限公司 | Improved synthesis method for dencichine |
| CN105439883A (en) * | 2015-12-11 | 2016-03-30 | 中国医学科学院药用植物研究所 | Preparation method and application of D-dencichine |
| CN109180532A (en) * | 2018-08-29 | 2019-01-11 | 南京天际联盟医药科技有限公司 | The high efficiency preparation method of D- dencichine |
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