CN115160192A - 2-guanidinoethane-1-sulfonic acid dioctadecyl ester, preparation method and application thereof - Google Patents
2-guanidinoethane-1-sulfonic acid dioctadecyl ester, preparation method and application thereof Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/69—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a carbon skeleton substituted by nitrogen atoms, not being part of nitro or nitroso groups
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/30—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reactions not involving the formation of esterified sulfo groups
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Abstract
The invention provides a preparation method of 2-guanidinoethane-1-sulfonic acid dioctadecyl ester, which comprises the following steps: s1, octacosanol is used as a raw material, and N-Boc-octacosyl taurate is generated with N-Boc-tauryl chloride under the alkaline condition of triethylamine; s2, carrying out deprotection on amino Boc group of N-Boc-octacosyl taurate under an acidic condition to generate octacosyl taurate; and S3, carrying out a reaction system of octacosyl taurate and cyanamide ethanol solution, and obtaining the 2-guanidinoethane-1-sulfonic acid dioctadecyl ester by adjusting the pH value, heating, preserving the temperature, cooling, adjusting the pH value again, cooling and crystallizing. The invention can improve the water solubility of octacosanol and increase the bioavailability thereof.
Description
Technical Field
The invention belongs to the field of chemical industry, and particularly relates to 2-guanidinoethane-1-sulfonic acid dioctadecyl ester, a preparation method and application thereof.
Background
Octacosanol belongs to higher fatty alcohol, is a natural bioactive substance extracted from wheat germ oil and the like, has multiple biological functions, and has the main physiological functions of: 1) Promoting reproductive protection function, and treating spermatogenic disorder; 2) Improving endurance, energy and physical strength; 3) Shortening the reaction time of the muscle nerve and improving the reaction sensitivity; 3) Promoting hormone function, and relieving muscle pain; 4) Improving myocardial function, and reducing systolic blood pressure; 5) Improving basal metabolic rate of organism. Octacosanol can be used for treating hypercalcemia osteoporosis, hypercholesterolemia and hyperlipoproteinemia, and stimulating sexual behavior of animals and human beings, and cosmetic containing octacosanol can promote skin blood circulation and activate cells, and has antiinflammatory and skin disease preventing and treating effects. The octacosanol has high safety, and the dosage of the octacosanol is small because the water solubility of higher fatty alcohol is poor, so that the octacosanol needs to be properly modified to increase the solubility of the octacosanol, thereby improving the bioavailability of the octacosanol.
Taurine, also known as taurine and ox bile element, is a sulfur-containing amino acid with simple structure in animal body. Taurine exists in free form in the human and mammal bodies in large quantities, is nontoxic to the human body, has no side effects, and is an amino acid essential to the human body. Has important effect on the development of the nervous system of the fetus and the infant. In addition, taurine can be widely applied to the fields of food additives, medicines, organic synthesis and the like, and taurine receives the guanyl group of arginine, generates guanidino taurine under the catalysis of ATP-guanyl transferase, and phosphorylates the guanyl group to generate guanidino taurine phosphate, which can be used as a phosphate source in lower animals and plays an important role in energy metabolism.
Zhejiang chemical industry, volume 37, 2006, 1 st research review on chemical and biological active ingredients in sipunculid animals indicates that: guanidyl taurine is present in several muscles of marine spirochaete including Phascolosoma elongatum, and extracted. U.S. Pat. No. 5, 3943253 GUANIDO ACIDS AS FUNGICIDES, reports on the use of amidino taurine AS a bactericide. Japanese patent jp58194812a コレステロール depurating agent studies the remarkable effect of amidino taurine in reducing liver cholesterol and cholesterol in blood, and amidino taurine exists in the living body and plays a very important role in the living body.
Disclosure of Invention
The invention aims to provide 2-guanidinoethane-1-sulfonic acid dioctadecyl ester, a preparation method and application thereof, improve the water solubility of octacosanol and increase the bioavailability of octacosanol.
In order to solve the above technical problems, an embodiment of the present invention provides a dioctadecyl 2-guanidinoethane-1-sulfonate, which has a chemical structural formula:
the invention also provides a preparation method of the 2-guanidinoethane-1-sulfonic acid dioctadecyl ester, which comprises the following steps:
s1, octacosanol is used as a raw material, and N-Boc-octacosyl taurate is generated with N-Boc-tauryl chloride under the alkaline condition of triethylamine;
s2, carrying out deprotection on amino Boc group of N-Boc-octacosyl taurate under an acidic condition to generate octacosyl taurate;
and S3, carrying out a reaction system of octacosyl taurate and cyanamide ethanol solution, and obtaining the 2-guanidinoethane-1-sulfonic acid dioctadecyl ester by adjusting the pH value, heating, preserving the temperature, cooling, adjusting the pH value again, cooling and crystallizing.
Wherein the synthesis reaction formula of the 2-guanidinoethane-1-sulfonic acid dioctadecyl ester is as follows:
the specific operation of step S1 is as follows:
octacosanol and N-Boc-tauryl chloride are used as raw materials, octacosanol is dissolved in N, N-dimethylformamide solution, triethylamine is added, the temperature is reduced to 0 ℃, N-Boc-tauryl chloride solution is dripped in, the temperature is gradually raised to room temperature for reaction for 5 to 10 hours, reaction liquid is flushed into ice water, an organic layer is separated, a water layer is washed twice by dichloromethane, washing liquid and the organic layer are combined, diluted hydrochloric acid is used for washing and water washing, saturated sodium chloride solution is used for washing, and N-Boc-octacosyl tauryl is synthesized.
Preferably, the amount of octacosanol and N-Boc-tauryl chloride is in a ratio of 1:2 to 1:5;
the mass ratio of the octacosanol to the triethylamine is 1:1-1:4.
The specific operation of step S2 is as follows:
cooling an ethyl acetate solution containing HCl to 0 ℃, adding the N-Boc-octacosyl taurate prepared in the step S1, gradually raising the temperature to room temperature for reaction for 2-6 hours, carrying out suction filtration on a reaction solution to obtain a solid, dissolving the solid with methanol to obtain a solid, adding isopropanol, recrystallizing to obtain a product, then using an NaOH aqueous solution, fully stirring, washing with water, and using Na for an organic layer 2 SO 4 Drying and concentrating to obtain octacosyl taurate.
Preferably, the HCl concentration in the HCl-containing ethyl acetate solution is 0.5mol/L to 2mol/L.
Wherein, step S3 includes the following steps:
s3.1, adding the octacosyl taurate obtained in the step S2 into ethanol, stirring and dispersing, and heating to 30-60 ℃ to dissolve the octacosyl taurate;
s3.2, adjusting the pH value to 7-11 by using alkali;
s3.3, heating the solution to 50-90 ℃, and dropwise adding a quantitative cyanamide aqueous solution with the mass concentration of 20-50%;
s3.4, after the dropwise addition of the cyanamide aqueous solution is finished, preserving the heat for 2-6 hours at the temperature of 50-90 ℃;
s3.5, after the heat preservation is finished, cooling to room temperature, and adjusting the pH value to be neutral or alkalescent by using acid;
s3.6, cooling to 5-15 ℃, separating out crystals, filtering, and washing a filter cake with absolute ethyl alcohol;
s3.7, carrying out vacuum drying on the washed crystal to obtain the 2-guanidinoethane-1-sulfonic acid dioctadecyl ester.
The invention also provides application of the 2-guanidinoethane-1-sulfonic acid dioctadecyl ester in preparing medicines for treating reproductive diseases, vascular diseases and cholesterol.
The invention also provides application of the 2-guanidinoethane-1-sulfonic acid dioctadecyl ester, which is used as a production raw material of bactericides and surfactants.
The technical scheme of the invention has the following beneficial effects: the invention greatly improves the water solubility of octacosanol, introduces a taurine structure into an octacosanol structure which is insoluble in water and further introduces a guanidyl structure, wherein guanidyl is an alkaline chemical group easy to hydrolyze, and can generate salt with acid to greatly improve the water solubility of octacosanol and improve the bioavailability. Octacosanol can treat dysgenesis diseases, taurine also has a promoting effect on reproduction, and the invention further improves the reproduction promoting effect and improves the sexual function. Meanwhile, the octacosanol of the invention introduces a taurine structure to further improve the physiological functions of the octacosanol, including the functions of enhancing physical strength and endurance capacity, protecting muscles and the like.
Detailed Description
In order to make the technical problems, technical solutions and advantages to be solved by the present invention clearer, the following detailed description is given with reference to specific embodiments.
The invention provides 2-guanidinoethane-1-sulfonic acid dioctadecyl ester, the chemical structural formula of which is as follows:
the preparation method of the 2-guanidinoethane-1-sulfonic acid dioctadecyl ester comprises the following steps:
s1, octacosanol is used as a raw material, and N-Boc-octacosyl taurate is generated with commercial N-Boc-tauryl chloride under the alkaline condition of triethylamine. The specific operation is as follows:
octacosanol and N-Boc-bovine sulfonyl chloride (Shanghai Shao reagent Co., ltd.) are used as raw materials, octacosanol is dissolved in N, N-Dimethylformamide (DMF) solution, triethylamine is added, the temperature is reduced to 0 ℃, N-Boc-bovine sulfonyl chloride solution is dripped in, the temperature is gradually raised to room temperature for reaction for 5 to 10 hours, reaction liquid is flushed into ice water, an organic layer is separated, a water layer is washed twice by dichloromethane, washing liquid and the organic layer are combined, diluted hydrochloric acid is used for washing and water washing, saturated sodium chloride solution is used for washing, and the N-Boc-octacosyl bovine sulfonate is synthesized.
Wherein the amount of octacosanol and N-Boc-tauryl chloride is in a ratio of 1:2 to 1:5, preferably 1:1; the mass ratio of the octacosanol to the triethylamine is 1:1-1:4, preferably 1:2.
And (3) carrying out amino Boc group deprotection on S2 and N-Boc-octacosyl taurate under an acidic condition to generate octacosyl taurate. The specific operation is as follows:
cooling 10mL of ethyl acetate solution () containing HCl to 0 ℃, adding the N-Boc-octacosyl taurate prepared in the step S1, gradually raising the temperature to room temperature for reaction for 2-6 hours, carrying out suction filtration on the reaction liquid to obtain a solid, dissolving the solid obtained by using methanol, adding isopropanol, recrystallizing to obtain a product, then using NaOH aqueous solution, fully stirring, washing with water, and using Na for an organic layer 2 SO 4 Drying and concentrating to obtain octacosyl taurate.
Wherein, the HCl-containing ethyl acetate solution is a solution formed by dissolving hydrogen chloride gas in ethyl acetate, and the concentration of HCl is 0.5 mol/L-2 mol/L.
And S3, carrying out a reaction system of octacosyl taurate and cyanamide ethanol solution, and obtaining the 2-guanidinoethane-1-sulfonic acid dioctadecyl ester by adjusting the pH value, heating, preserving the temperature, cooling, adjusting the pH value again, cooling and crystallizing. The specific operation is as follows:
s3.1, adding the octacosyl taurate obtained in the step S2 into ethanol, stirring and dispersing, and heating to 30-60 ℃ to dissolve, preferably 40 ℃;
s3.2, adjusting the pH value to 7-11, preferably 9 by using alkali, wherein liquid ammonia, sodium hydroxide and solution thereof, and sodium bicarbonate solution can be used as the alkali.
S3.3, heating the solution to 50-90 ℃, and dropwise adding a quantitative cyanamide aqueous solution with the mass concentration of 20-50%; wherein the mass ratio of octacosanol to cyanamide is 1:2-3:2, preferably 1:1; the concentration of cyanamide may be 20% to 50%, preferably 30%.
S3.4, after the dropwise addition of the cyanamide aqueous solution is finished, preserving the heat for 2-6 hours, preferably 3 hours at the temperature of 50-90 ℃;
s3.5, after the heat preservation is finished, cooling to room temperature, and adjusting the pH value to be neutral or alkalescent by using acid, wherein the acid can be inorganic acid such as hydrochloric acid or organic acid acetic acid and the like;
s3.6, cooling to 5-15 ℃, separating out crystals, filtering, and washing a filter cake with absolute ethyl alcohol;
s3.7, carrying out vacuum drying on the washed crystal to obtain the 2-guanidinoethane-1-sulfonic acid dioctadecyl ester.
The synthesis reaction formula of the 2-guanidinoethane-1-sulfonic acid dioctadecyl ester is as follows:
the invention also provides application of the 2-guanidinoethane-1-sulfonic acid dioctadecyl ester in preparing medicines for treating reproductive diseases, vascular diseases and cholesterol.
The application of the 2-guanidinoethane-1-sulfonic acid dioctadecyl ester can also be used for the production of chemical raw materials such as bactericides, surfactants and the like.
The technical solution of the present invention is further illustrated below with reference to several specific examples.
Example 1
Step 1:
octacosanol (0.2mmol, 82mg) is dissolved in 20mL of N, N-Dimethylformamide (DMF) solution, triethylamine (0.4 mmol) is added, the temperature is reduced to 0 ℃, N-Boc-taurine chloride (0.2mmol, 48.6 mg) solution is dripped in, the temperature is gradually increased to room temperature for reaction for 7 hours, the reaction solution is flushed into ice water, an organic layer is separated, a water layer is washed twice by dichloromethane, a washing solution and the organic layer are combined, washed by dilute hydrochloric acid, washed by water, washed by saturated sodium chloride solution, and the N-Boc-octacosyl taurine ester is synthesized, wherein the yield is 85%.
Step 2:
cooling lmol/L ethyl acetate solution containing HCl (10 mL, the ethyl acetate solution containing HCl is a solution formed by dissolving hydrogen chloride gas in ethyl acetate) to 0 ℃, adding N-Boc-octacosyl taurate, gradually raising the temperature to room temperature for reaction for 4 hours, carrying out suction filtration on reaction liquid to obtain a solid, dissolving the solid with methanol, adding isopropanol, recrystallizing to obtain a product, then fully stirring with NaOH aqueous solution, washing with water, and using Na for an organic layer 2 SO 4 Drying and concentrating to obtain the target compound octacosyl taurate with the yield of 90 percent.
And step 3:
50mL of ethanol is added into a 100mL four-neck flask, 51.7mg (0.1 mmol) of octacosyl taurate is added, the mixture is stirred and dispersed, the temperature is raised to 40 ℃ to be dissolved, 30% of sodium hydroxide is dropwise added to adjust the pH value of the solution to be 9.0, the temperature is raised to 70 ℃, 13.75mg (0.1 mol) of 30% cyanamide is dropwise added, after the dropwise addition is finished, the temperature is kept for 3 hours, the temperature is reduced to 30 ℃, the pH value is adjusted to 7.5 by 30% of hydrochloric acid, the temperature is continuously reduced to 5 ℃, the filtration is carried out, and the drying is carried out under the vacuum condition of 60 ℃ to obtain 43.6mg of the product with the yield of 78%. Elemental analysis of the product showed C66.48%; h11.68 percent; n7.49%; o8.64 percent; s5.71% and theoretical C66.50%; h11.70 percent; n is 7.50 percent; o8.57 percent; s5.73% consistent.
Example 2
Step 1:
octacosanol (0.2mmol, 82mg) is dissolved in 20mL of N, N-Dimethylformamide (DMF) solution, triethylamine (0.2 mmol) is added, the temperature is reduced to 0 ℃, N-Boc-taurine chloride (0.4mmol, 97.2mg) solution is dripped in, the temperature is gradually raised to room temperature for reaction for 4 hours, the reaction solution is flushed into ice water, an organic layer is separated, a water layer is washed twice by dichloromethane, washing liquid and the organic layer are combined, diluted hydrochloric acid is used for washing, water washing is carried out, saturated sodium chloride solution is used for washing, and N-Boc-octacosyl taurine ester is synthesized, wherein the yield is 63%.
Step 2:
cooling 0.5mol/L HCl-containing ethyl acetate solution (10 mL, the HCl-containing ethyl acetate solution is a solution formed by dissolving hydrogen chloride gas in ethyl acetate) to 0 ℃, adding N-Boc-octacosyl taurate, gradually raising the temperature to room temperature for reaction for 2 hours, carrying out suction filtration on reaction liquid to obtain a solid, dissolving the solid with methanol to obtain a solid, adding isopropanol, recrystallizing to obtain a product, then using NaOH aqueous solution, fully stirring, washing with water, and using Na for an organic layer 2 SO 4 Drying and concentrating to obtain the target compound octacosyl taurate with the yield of 71 percent.
And step 3:
50mL of ethanol is added into a 100mL four-neck flask, 51.7mg (0.1 mmol) of octacosyl taurate is added, the mixture is stirred and dispersed, the temperature is raised to 30 ℃ to be dissolved, 30% of sodium hydroxide is dropwise added to adjust the pH value of the solution to be 7.0, the temperature is raised to 50 ℃, 13.75mg (0.1 mol) of 20% cyanamide is dropwise added, after the dropwise addition is finished, the temperature is kept for 2 hours, the temperature is lowered to 30 ℃, 30% of hydrochloric acid is used for adjusting the pH value to be 7.5, the temperature is continuously lowered to 5 ℃, the filtration is carried out, and the drying is carried out under the vacuum condition at 60 ℃ to obtain 23.5mg of the product, wherein the yield is 42%. The product is subjected to elemental analysis, wherein C is 66.55%; h11.75 percent; n is 7.50 percent; o8.45 percent; 5.75 percent of S and 66.50 percent of theoretical C; h11.70%; n is 7.50 percent; o8.57 percent; s5.73% consistent.
Example 3
Step 1:
octacosanol (0.2mmol, 82mg) is dissolved in 20mL of N, N-Dimethylformamide (DMF) solution, triethylamine (0.8 mmol) is added, the temperature is reduced to 0 ℃, N-Boc-taurine chloride (0.04mmol, 9.72mg) solution is dropped into the solution, the solution is gradually raised to the room temperature to react for 4 hours, the reaction solution is flushed into ice water, an organic layer is separated, a water layer is washed twice by dichloromethane, washing liquid and the organic layer are combined, diluted hydrochloric acid is used for washing, water washing is carried out, saturated sodium chloride solution is used for washing, and the N-Boc-octacosyl taurine ester is synthesized, wherein the yield is 18%.
Step 2:
cooling 2mol/L HCl-containing ethyl acetate solution (10 mL, the HCl-containing ethyl acetate solution is a solution formed by dissolving hydrogen chloride gas in ethyl acetate) to 0 ℃, adding N-Boc-octacosyl taurate, gradually raising the temperature to room temperature for reaction for 6 hours, carrying out suction filtration on reaction liquid to obtain a solid, dissolving the solid with methanol, adding isopropanol, recrystallizing to obtain a product, then using NaOH aqueous solution, fully stirring, washing with water, and using Na for an organic layer 2 SO 4 Drying and concentrating to obtain the target compound octacosyl taurate with the yield of 59 percent.
And step 3:
50mL of ethanol is added into a 100mL four-neck flask, 51.7mg (0.1 mmol) of octacosyl taurate is added, the mixture is stirred and dispersed, the temperature is raised to 60 ℃ to be dissolved, 30% of sodium hydroxide is dropwise added to adjust the pH value of the solution to be 11.0, the temperature is raised to 90 ℃, 8.28mg (0.06 mol) of 50% cyanamide is dropwise added, after the dropwise addition is finished, the temperature is kept for 6 hours, the temperature is lowered to 30 ℃, 30% of hydrochloric acid is used for adjusting the pH value to be 7.5, the temperature is continuously lowered to 15 ℃, the filtration is carried out, and the drying is carried out under the vacuum condition at 60 ℃ to obtain 15.6mg of the product with the yield of 28%. Elemental analysis of the product showed C66.52%; h11.72 percent; n is 7.50 percent; o8.55 percent; 5.71 percent of S and 66.50 percent of theoretical C; h11.70 percent; n is 7.50 percent; o8.57 percent; s5.73% consistent.
While the foregoing is directed to the preferred embodiment of the present invention, it will be understood by those skilled in the art that various changes and modifications may be made without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (10)
1. A2-guanidinoethane-1-sulfonic acid dioctadecyl ester is characterized in that the chemical structural formula is as follows:
2. a preparation method of 2-guanidinoethane-1-sulfonic acid dioctadecyl ester is characterized by comprising the following steps:
s1, octacosanol is used as a raw material, and N-Boc-octacosyl taurate is generated with N-Boc-tauryl chloride under the alkaline condition of triethylamine;
s2, carrying out deprotection on amino Boc group of N-Boc-octacosyl taurate under an acidic condition to generate octacosyl taurate;
and S3, carrying out a reaction system of octacosyl taurate and cyanamide ethanol solution, and obtaining the 2-guanidinoethane-1-sulfonic acid dioctadecyl ester by adjusting the pH value, heating, preserving the temperature, cooling, adjusting the pH value again, cooling and crystallizing.
3. The process for producing dioctadecyl 2-guanidinoethane-1-sulfonate according to claim 2, wherein the synthesis reaction formula is as follows:
4. the process for the preparation of dioctadecyl 2-guanidinoethane-1-sulfonate according to claim 2, characterized in that the specific operation of step S1 is as follows:
octacosanol and N-Boc-tauryl chloride are used as raw materials, octacosanol is dissolved in N, N-dimethylformamide solution, triethylamine is added, the temperature is reduced to 0 ℃, N-Boc-tauryl chloride solution is dripped in, the temperature is gradually raised to room temperature for reaction for 5 to 10 hours, reaction liquid is flushed into ice water, an organic layer is separated, a water layer is washed twice by dichloromethane, washing liquid and the organic layer are combined, diluted hydrochloric acid is used for washing and water washing, saturated sodium chloride solution is used for washing, and N-Boc-octacosyl tauryl is synthesized.
5. The method for preparing dioctadecyl 2-guanidinoethane-1-sulfonate according to claim 2 or 4, wherein the amount ratio of the octacosanol and the N-Boc-tauryl chloride is 1:2-1:5;
the mass ratio of the octacosanol to the triethylamine is 1:1-1:4.
6. The process for the preparation of dioctadecyl 2-guanidinoethane-1-sulfonate according to claim 2, characterized in that the specific operation of step S2 is as follows:
cooling an ethyl acetate solution containing HCl to 0 ℃, adding the N-Boc-octacosyl taurate prepared in the step S1, gradually raising the temperature to room temperature for reaction for 2-6 hours, carrying out suction filtration on a reaction solution to obtain a solid, dissolving the solid with methanol to obtain a solid, adding isopropanol, recrystallizing to obtain a product, then using an NaOH aqueous solution, fully stirring, washing with water, and using Na for an organic layer 2 SO 4 Drying and concentrating to obtain octacosyl taurate.
7. The process for producing dioctadecyl 2-guanidinoethane-1-sulfonate according to claim 2 or 6, wherein the concentration of HCl in the ethyl acetate solution containing HCl is 0.5mol/L to 2mol/L.
8. The method for preparing dioctadecyl 2-guanidinoethane-1-sulfonate according to claim 2, wherein step S3 comprises the steps of:
s3.1, adding the octacosyl taurate obtained in the step S2 into ethanol, stirring and dispersing, and heating to 30-60 ℃ to dissolve the octacosyl taurate;
s3.2, adjusting the pH value to 7-11 by using alkali;
s3.3, heating the solution to 50-90 ℃, and dropwise adding a quantitative cyanamide aqueous solution with the mass concentration of 20-50%;
s3.4, after the dropwise addition of the cyanamide aqueous solution is finished, keeping the temperature at 50-90 ℃ for 2-6 hours;
s3.5, after the heat preservation is finished, cooling to room temperature, and adjusting the pH value to be neutral or alkalescent by using acid;
s3.6, cooling to 5-15 ℃, separating out crystals, filtering, and washing a filter cake with absolute ethyl alcohol;
s3.7, carrying out vacuum drying on the washed crystal to obtain the 2-guanidinoethane-1-sulfonic acid dioctadecyl ester.
9. The application of the 2-guanidinoethane-1-sulfonic acid dioctadecyl ester is characterized in that the 2-guanidinoethane-1-sulfonic acid dioctadecyl ester is used for preparing medicines for treating reproductive diseases, vascular diseases and cholesterol.
10. The application of the 2-guanidinoethane-1-sulfonic acid dioctadecyl ester is characterized in that the 2-guanidinoethane-1-sulfonic acid dioctadecyl ester is used as a production raw material of bactericides and surfactants.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1153751A (en) * | 1956-06-06 | 1958-03-21 | Gen Aniline & Film Corp | Process for the preparation of anionic surfactants of the ester and amide type |
| GB799909A (en) * | 1956-05-11 | 1958-08-13 | Gen Aniline & Film Corp | Improved process of preparing ester and amide type anionic surface active agents |
| US4071543A (en) * | 1975-08-26 | 1978-01-31 | Bayer Aktiengesellschaft | Process for the preparation of acyltaurides |
| WO1986003944A1 (en) * | 1985-01-03 | 1986-07-17 | Joyce Patrick J | Heat stabilized peptide table salt substitutes |
| CN101108323A (en) * | 2006-07-20 | 2008-01-23 | 中国科学院理化技术研究所 | N-(alpha- aryloxy group)acyl group taurine salt surfactant and method of preparing the same and use thereof |
| WO2015067785A1 (en) * | 2013-11-08 | 2015-05-14 | L'oreal | Cosmetic compositions comprising spiculisporic acid and at least one sulfate and/or sulfonate surfactant |
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2022
- 2022-08-02 CN CN202210918713.0A patent/CN115160192A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB799909A (en) * | 1956-05-11 | 1958-08-13 | Gen Aniline & Film Corp | Improved process of preparing ester and amide type anionic surface active agents |
| FR1153751A (en) * | 1956-06-06 | 1958-03-21 | Gen Aniline & Film Corp | Process for the preparation of anionic surfactants of the ester and amide type |
| US4071543A (en) * | 1975-08-26 | 1978-01-31 | Bayer Aktiengesellschaft | Process for the preparation of acyltaurides |
| WO1986003944A1 (en) * | 1985-01-03 | 1986-07-17 | Joyce Patrick J | Heat stabilized peptide table salt substitutes |
| CN101108323A (en) * | 2006-07-20 | 2008-01-23 | 中国科学院理化技术研究所 | N-(alpha- aryloxy group)acyl group taurine salt surfactant and method of preparing the same and use thereof |
| WO2015067785A1 (en) * | 2013-11-08 | 2015-05-14 | L'oreal | Cosmetic compositions comprising spiculisporic acid and at least one sulfate and/or sulfonate surfactant |
| CN105705132A (en) * | 2013-11-08 | 2016-06-22 | 欧莱雅 | Thermoplastic fluorinated polymer composition for off-shore pipes |
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