CN119775163A - (S) -3-aminobutyric acid hydrochloride compound and preparation method thereof - Google Patents
(S) -3-aminobutyric acid hydrochloride compound and preparation method thereof Download PDFInfo
- Publication number
- CN119775163A CN119775163A CN202411481802.9A CN202411481802A CN119775163A CN 119775163 A CN119775163 A CN 119775163A CN 202411481802 A CN202411481802 A CN 202411481802A CN 119775163 A CN119775163 A CN 119775163A
- Authority
- CN
- China
- Prior art keywords
- compound
- reaction
- aminobutyric acid
- acid hydrochloride
- producing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明公开了一种(S)‑3‑氨基丁腈盐酸盐类化合物的制备方法，包括如下步骤：S1氯化反应：在反应溶剂中，加入氯化亚砜，催化剂，控制一定的温度下，滴加化合物1，滴加完毕，在一定的温度度下反应，滴加至水中淬灭，得化合物2的水溶液；S2氰化反应：将化合物2加入到反应溶剂中，加入30％氰化钠溶液，控制一定的温度，反应一定的时间，反应结束后，萃取分层，有机相使用氯化钠溶液洗涤，浓缩得到化合物5；S3成盐反应：将HCl(gas)有机溶剂的溶液滴加到化合物5的有机溶剂中，控制一定的温度，反应一定的时间，反应结束后，降温，过滤，干燥，得到目标化合物6。本发明以68.5％摩尔收率得到(S)‑3‑氨基丁腈盐酸盐，成本低，具有很强的成本竞争力。
The invention discloses a method for preparing a (S)-3-aminobutyronitrile hydrochloride compound, comprising the following steps: S1 chlorination reaction: in a reaction solvent, thionyl chloride and a catalyst are added, and a certain temperature is controlled, and compound 1 is added dropwise, and the addition is completed, and the reaction is carried out at a certain temperature, and the compound 2 is added dropwise to water for quenching to obtain an aqueous solution; S2 cyanidation reaction: compound 2 is added to a reaction solvent, 30% sodium cyanide solution is added, a certain temperature is controlled, and a certain time of reaction is carried out, and after the reaction is completed, extraction and stratification are performed, and the organic phase is washed with a sodium chloride solution, and concentrated to obtain compound 5; S3 salt-forming reaction: a solution of HCl (gas) organic solvent is added dropwise to an organic solvent of compound 5, a certain temperature is controlled, and a certain time of reaction is carried out, and after the reaction is completed, the temperature is lowered, filtered, and dried to obtain a target compound 6. The present invention obtains (S)-3-aminobutyronitrile hydrochloride with a molar yield of 68.5%, and the cost is low, and the cost competitiveness is very strong.
Description
Technical Field
The invention relates to the technical field of medicine synthesis and preparation, in particular to an (S) -3-amino butyronitrile hydrochloride compound and a preparation method thereof.
Background
Orforglipron is an oral GLP-1 small molecule agonist developed by Gift corporation, is used for treating obesity and type II diabetes, and is the fastest growing oral GLP-1 receptor agonist with the current research progress in clinical stage III. The market demand is great for (S) -3-aminobutyronitrile hydrochloride as an intermediate for the drug erbelix (Orforglipron). However, the conventional synthesis method in the existing (S) -3-amino butyronitrile hydrochloride synthesis process has the disadvantages of complex operation process, high cost, small energy production and low atom utilization rate, and a new efficient and simple synthesis method needs to be developed in order to meet the market demands.
The published synthetic method of (S) -3-amino butyronitrile hydrochloride can be seen in patent CN116390926, in the route, compound 2-A is taken as a starting material, and is substituted by MsCl and reacts with Boc to prepare compound 2-B, compound 2-B is subjected to cyanidation to obtain compound 2-C, and compound 2-C is subjected to Boc removal to obtain target product compound 2-D, wherein the reaction route is as follows:
the method has the defects that toxic reagents (MsCl) are used, the reaction is required to be carried out at low temperature, the heat release in the reaction process is serious, the post-treatment operation is complicated, the process cost is high, the equipment utilization rate is low, the productivity is low, and the large-scale industrial production is not facilitated.
Disclosure of Invention
The invention provides the (S) -3-amino butyronitrile hydrochloride compound and the preparation method thereof, which are used for solving the defects in the prior art, and the method has the advantages of high conversion rate, high yield, simple operation, low cost and suitability for industrial production.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
the preparation method of the (S) -3-aminobutyric acid hydrochloride compound comprises the following steps:
S1, chloridizing reaction, namely adding thionyl chloride and a catalyst into a reaction solvent, dropwise adding a compound 1 at a certain temperature, reacting for a certain time at a certain temperature after the dropwise adding, dropwise adding into water and quenching to obtain an aqueous solution of a compound 2, wherein the reaction formula is as follows:
S2, cyanide reaction, namely adding the compound 2 into a reaction solvent, adding 30% sodium cyanide solution, controlling a certain temperature, reacting for a certain time, extracting and layering after the reaction is finished, washing an organic phase by using the sodium chloride solution, and concentrating to obtain a compound 5, wherein the reaction formula is as follows:
S3, salifying reaction, namely dropwise adding a solution of HCl (gas) organic solvent into the organic solvent of the compound 5, controlling a certain temperature, reacting for a certain time, cooling, filtering and drying after the reaction is finished to obtain a target compound 6, wherein the reaction formula is as follows:
Wherein r1=me, et, OMe, OEt, r2=h, boc.
Preferably, step S11 is further included between step S1 and step S2:
The cyclization reaction is to drop the compound 2 aqueous solution into the sodium hydroxide aqueous solution, control certain temperature, react for a certain time, get the compound 4 aqueous solution after the reaction is finished, compound 4 reacts again through step S2 to get the compound 5, the total reaction formula is as follows:
Preferably, step S111 is further included between step S1 and step S11:
The substitution reaction comprises the steps of S11 obtaining a compound 3, adding di-tert-butyl dicarbonate into the compound 3, controlling a certain temperature, reacting for a certain time, extracting and layering after the reaction is finished, washing an organic phase by using a sodium chloride aqueous solution, and concentrating to obtain a compound 4, wherein the total reaction formula is as follows:
Further, the reaction solvent in step S1 is any one or more solvents selected from dichloromethane, tetrahydrofuran, methyltetrahydrofuran, chloroform, dichloroethane, and the like.
Further, the reaction temperature in the step S1 is 20-80 ℃.
Further, in the step S1, the ratio of the compound 1, the thionyl chloride and the reaction solvent is 1W to 2.4W to 8W. Wherein W refers to mass percent (WEIGHTPERCENT), and the ratio values W appearing in the specification refer to mass percent without specific explanation.
Further, the reaction temperature in the step S11 is 20-70 ℃.
Further, in the step S11, the ratio of the compound 2 to the sodium hydroxide to the water is 1W:1.08-3.6W:2.52W.
Further, the ratio of the compound 3, di-tert-butyl dicarbonate and water in the step S111 is 1W:3.1W:2.7W.
Further, in step S111, the extraction solvent for the extraction and delamination is at least one of ethyl acetate, dichloromethane, and other solvents.
Further, the reaction solvent in the step S2 is at least one of DMF, DMSO and tetrahydrofuran. DMF refers to N, N-dimethylformamide having the chemical formula CH 3CON(CH3)2, DMSO refers to dimethyl sulfoxide having the chemical formula (CH 3)2 SO.
Further, in the step S2, the solvent is doubled to be 3-10W.
Further, the reaction temperature in the step S2 is 20-80 ℃.
Further, the organic solvent in step S3 is any one or more of ethyl acetate, 1, 4-dioxane solution, methanol, ethanol, and the like.
Further, the HCl (gas) organic solvent in the step S3 is at least one of ethyl acetate solution of HCl (gas), 1, 4-dioxane solution of HCl (gas), methanol solution of HCl (gas), ethanol solution of HCl (gas) and the like.
The invention also discloses the (S) -3-amino butyronitrile hydrochloride compound prepared by the preparation method of the (S) -3-amino butyronitrile hydrochloride compound.
The beneficial effects of the invention are as follows:
the synthesis route reported in the patent (CN 116390926) needs to use the drug MsCl for hydroxyl protection, has the risk of introducing basic toxin impurities, and needs low-temperature equipment during workshop production, has complex process and high cost, and the invention designs a brand new process route, and the (S) -3-amino butyronitrile hydrochloride is obtained with the molar yield of 68.5% through the steps of chlorination, cyclization, boc protection, cyanidation, boc salt formation and the like, thereby having low cost, strong cost competitiveness, mild reaction conditions, simple reaction, good selectivity and easy amplification and being suitable for industrial production.
Drawings
FIG. 1 is a carbon spectrum of compound 2 obtained in example 2 of the present invention;
FIG. 2 is a hydrogen spectrum of the compound 2 obtained in example 2 of the present invention;
FIG. 3 is a carbon spectrum of compound 5 obtained in example 4 of the present invention;
FIG. 4 is a hydrogen spectrum of the compound 5 obtained in example 4 of the present invention;
FIG. 5 is a carbon spectrum of compound 6 obtained in example 5 of the present invention;
FIG. 6 is a hydrogen spectrum of Compound 6 obtained in example 5 of the present invention.
Detailed Description
The present invention will be described in further detail with reference to specific embodiments thereof in order to enable those skilled in the art to better understand the technical aspects of the invention.
The invention relates to a preparation method and application of an (S) -3-aminobutyric acid hydrochloride compound. The compound is mainly used for preparing a new drug Orforglipron, orforglipron is an oral GLP-1 small molecule agonist, is used for treating obesity and type II diabetes, relates to the technical field of medicine synthesis and preparation, and comprises the following synthesis steps:
The invention has three reaction routes for obtaining the compound 6, namely, the following reaction route 1 is adopted, wherein (1) the compound 1 is taken as an initial reaction raw material, the compound 2 is obtained through chlorination reaction, (2) the compound 2 is generated to form a compound 3 under alkaline conditions, (3) the compound 3 is reacted with di-tert-butyl dicarbonate to form a compound 4, (4) the compound 4 is subjected to ring opening by sodium cyanide to obtain a compound 5, and (5) the compound 5 is subjected to Boc removal to form salt to obtain the target compound 6;
The reaction route 2 comprises (1) taking the compound 1 as an initial reaction raw material, carrying out chlorination reaction to obtain a compound 2, (2) carrying out ring opening on the compound 2 by sodium cyanide to obtain a compound 5, and (3) salifying the compound 5 to obtain a compound 6;
The reaction route 3 comprises (1) taking the compound 1 as an initial reaction raw material, carrying out chlorination reaction to obtain a compound 2, (2) generating a compound 4 by the compound 2 under alkaline conditions, (3) carrying out ring opening on the compound 4 by sodium cyanide to obtain a compound 5, and (4) salifying the compound 5 to obtain a compound 6;
the reaction formula is as follows:
wherein when R2 is H, compound 4 is identical to compound 3 in structural formula.
The invention takes the (S) - (+) -2-amino-1-propanol as the initial raw material, has the total yield of 68.5 percent through 5 steps of reaction, has simple reaction, good selectivity and lower cost, and is suitable for industrial production.
The above is a specific summary of the invention, and the reaction steps will be further described by way of specific examples.
Example 1 (preparation of (2R) -1-chloropropane-2-amino hydrochloride)
Adding chloroform (720.0 g, 8.0W), N, N-dimethylformamide (1.75 g, 0.02W), thionyl chloride (213.8 g, 2.4W), heating to 40-50 ℃, slowly dropwise adding L-aminopropanol (compound 1) (90.0 g, 1.0W) into a reaction bottle, reacting for 24 hours under heat preservation, adding the reaction liquid drop into water (180.0 g, 2.0W) after the reaction is finished, stirring and cooling to 10-30 ℃ for quenching reaction, extracting and layering, reserving an upper water phase, adding activated carbon (4.5 g, 0.05W), decoloring and press-filtering, leaching a filter cake with water (45 g, 0.5W), obtaining a compound 2, namely (2R) -1-chloropropane-2-amino hydrochloride aqueous solution, directly carrying out the next feeding, wherein the purity is 96 percent, and the yield is 98 percent.
Example 2 (preparation of (S) -2-methylaziridine)
Adding 30% caustic soda liquid (559.3 g, 3.6W) into a reaction bottle, cooling to 0-10 ℃, dropwise adding all compound 2 (155.8,1W) aqueous solution, controlling the temperature to 40-50 ℃ after the dropwise adding is finished, carrying out heat preservation reaction for 1h, cooling to 20-30 ℃ after the reaction is finished, and obtaining compound 3, namely (S) -2-methyl aziridine aqueous solution, wherein the purity is 99% and the yield is 98%.
Example 3 (preparation of (S) -2-methylaziridine-1-carboxylic acid tert-butyl ester
The reaction flask was charged with the aqueous solution of the entire compound 3 ((S) -2-methylaziridine) (68.4 g, 1.0W), the temperature was controlled at 25 to 35℃and di-tert-butyl dicarbonate (209.2 g, 3.1W) was added dropwise thereto, the reaction was continued for 2 hours, and after the completion of the reaction, the mixture was filtered and the cake was treated with ethyl acetate (287.3,4.2W)
Eluting, collecting filtrate, layering the filtrate, collecting an organic phase, washing the organic phase with a 10% sodium chloride aqueous solution (205.2 g, 3.0W), collecting the organic phase by liquid separation, concentrating the organic phase under reduced pressure at a temperature of 40-50 ℃ and a vacuum degree of-0.085 to-0.095 MPa until no fraction is distilled off, cooling to 20-30 ℃ to obtain a compound 4, namely (S) -2-methylaziridine-1-carboxylic acid tert-butyl ester concentrated solution, namely light yellow oily matter, wherein the purity is 99 percent and the yield is 80 percent;
Example 4 (preparation of tert-butyl [ (2S) -1-cyano-2-propyl ] carbamate)
Adding a compound 4 ((S) -2-methylaziridine-1-carboxylic acid tert-butyl ester) (130.0 g, 1.0W), adding N, N-dimethylamide (560.0 g, 4.3W), stirring to dissolve, adding 30% sodium cyanide (135.2 g, 1.04W) water solution, stirring and heating to 40-50 ℃, keeping the temperature for 16h, cooling to 20-30 ℃ after the reaction is finished, adding tap water (650.0 g, 5.0W), ethyl acetate (390.0 g, 3.0W), extracting and layering, collecting an organic phase, extracting the water phase with ethyl acetate, merging the organic phase, washing the organic phase with a 10% sodium chloride (390.0 g, 3.0W) 2 water solution, collecting the organic phase, controlling the temperature to 40-50 ℃ and vacuum degree to 0.08-0.1 MPa, concentrating the organic phase under reduced pressure until a large amount of white solid appears, slowly dropwise adding N-heptane (650.g, 5.5 h), stirring and slowly eluting the mixture for 1-30 h, stirring and cooling to 0.0 ℃ until the purity of the N-heptane (2-propyl acetate) is higher than that the N-butyl acetate is equal to 5.0%, and the N-butyl acetate is equal to 5-5% (2 g, 5% of the amino group) is obtained.
Example 5 (preparation of (S) -3-aminobutyronitrile hydrochloride
Adding a compound 5 ([ (2S) -1-cyano-2-propyl ] tert-butyl carbamate) (110.0 g,1.0 eq) and ethyl acetate (330.0 g, 3.0W) into a reaction bottle, dropwise adding a 14.5-20% ethyl hydrogen chloride solution (373.5 g,2.5 eq) at a temperature of 25+/-5 ℃, stirring for 2 h+/-10 min under heat preservation, cooling to 0-10 ℃ after the reaction,
Filter pressing, leaching with 0-10 ℃ ethyl acetate (55.0 g, 0.5W), obtaining crude product, adding ethyl acetate (550.0 g, 5.0W), cooling to 0-10 ℃, stirring for 1h, filter pressing, leaching filter cake with 0-10 ℃ ethyl acetate (55.0 g, 0.5W), obtaining compound 6 ((S) -3-amino butyronitrile hydrochloride), white to off-white solid, purity: 99%, yield 95%.
Example 6 (preparation of (S) -3-aminobutyronitrile)
Adding a compound 2 ((2R) -1-chloropropane-2-amino hydrochloride) (130.0 g, 1.0W), adding N, N-dimethylamide (560.0 g, 4.3W), stirring to dissolve, adding 30% sodium cyanide (135.2 g, 1.04W) water solution, stirring and heating to 40-50 ℃, keeping the temperature for 16h, cooling to 20-30 ℃ after the reaction is finished, adding tap water (650.0 g, 5.0W), ethyl acetate (390.0 g, 3.0W), extracting and layering, collecting an organic phase, extracting the water phase with ethyl acetate, merging the organic phase, washing the organic phase with a 10% sodium chloride (390.0 g, 3.0W) water solution twice, collecting the organic phase, controlling the temperature to 40-50 ℃, vacuum degree to 0.08-0.1 MPa, concentrating the organic phase under reduced pressure until a large amount of white solid appears, slowly dripping N-heptane (650.g, 5.0W), stirring for 1h, cooling to 0.0 ℃ slowly, cooling to 0.0 ℃ with tap water (650.0 g, 5.0W), filtering, cooling to obtain a crude product, and filtering to obtain a filter cake (20.0-0 g, 20.65% of N-heptane, 20.0% of the crude product, wherein the crude product is obtained by mixing the crude product, wherein the crude product is obtained by dripping the crude product.
Example 7 (preparation of (S) -3-aminobutyronitrile)
Adding a compound 4 ((S) -2-methylaziridine) (130.0 g, 1.0W), adding an N, N-dimethylamide (560.0 g, 4.3W) aqueous solution, stirring and clearing, adding a 30% sodium cyanide (135.2 g, 1.04W) aqueous solution, stirring and heating to 40-50 ℃, keeping the temperature for 16 hours, cooling to 20-30 ℃ after the reaction is finished, adding tap water (650.0 g, 5.0W), ethyl acetate (390.0 g, 3.0W), extracting and layering, collecting an organic phase, extracting the aqueous phase by using ethyl acetate, merging the organic phase, washing the organic phase twice by using a 10% sodium chloride (390.0 g, 3.0W) aqueous solution, collecting the organic phase, controlling the temperature to 40-50 ℃, vacuum degree to 0.08-0.1 MPa, concentrating the organic phase to a large amount of white solid, slowly dropwise adding N-heptane (650.0 g, 5.0W), stirring and slowly cooling to 0-10 ℃ for 0.5.10 hours, leaching, cooling to 0.0.0 ℃ and filtering, filtering and filtering to obtain a crude product ((S) -2.0.0W), filtering and filtering the crude product, wherein the crude product is obtained by dropwise adding the N-heptane (0.0 ℃ to 20% of the crude product, 20-5.0W) into the crude product.
The nuclear magnetic data of compound 2 are as follows:
1HNMR(400MHz,D2O)δ3.87-3.92(m,1H),3.71-3.78(m,2H),1.38(d,J＝8.0Hz,3H),3.8(d,J＝12.0,8.1Hz,1H)ppm.
the nuclear magnetic data of compound 5 are as follows:
1HNMR(400MHz,CDCl3)δ4.77(s,1H),3.94-4.00(m,1H),2.76(dd,J＝16.5,4.2Hz,1H),2.54(dd,J＝16.0,4.0Hz,1H),1.46(s,9H),1.33(d,J＝6.9Hz,3H)ppm;MS：m/z＝184(GC).
the nuclear magnetic data of compound 6 are as follows:
1HNMR(400MHz,DMSO-d6)δ8.60(s,2H),3.55(m,1H),3.06(dd,J＝16.1,16.1,1H),2.94(dd,J＝16.1,16.1,1H),1.34(d,J＝8.0Hz,3H)ppm,MS：m/z＝84(GCMS).
The foregoing is merely a preferred embodiment of the present invention, and it should be noted that the above-mentioned preferred embodiment should not be construed as limiting the invention, and the scope of the invention should be defined by the appended claims. It will be apparent to those skilled in the art that various modifications and adaptations can be made without departing from the spirit and scope of the invention, and such modifications and adaptations are intended to be comprehended within the scope of the invention.
Claims (16)
1. A method for preparing (S) -3-amino butyronitrile hydrochloride compounds, which is characterized by comprising the following steps:
S1, chloridizing reaction, namely adding thionyl chloride and a catalyst into a reaction solvent, dropwise adding a compound 1 at a certain temperature, reacting for a certain time at a certain temperature after the dropwise adding is finished, dropwise adding the obtained product into water, and quenching to obtain an aqueous solution of a compound 2, wherein the reaction formula is as follows:
S2, cyanide reaction, namely adding the compound 2 into a reaction solvent, adding 30% sodium cyanide solution, controlling a certain temperature, reacting for a certain time, extracting and layering after the reaction is finished, washing an organic phase by using the sodium chloride solution, and concentrating to obtain a compound 5, wherein the reaction formula is as follows:
S3, salifying reaction, namely dropwise adding a solution of HCl (gas) organic solvent into the organic solvent of the compound 5, controlling a certain temperature, reacting for a certain time, cooling, filtering and drying after the reaction is finished to obtain a target compound 6, wherein the reaction formula is as follows:
Wherein r1=me, et, OMe, OEt, r2=h, boc.
2. The method for producing (S) -3-aminobutyric acid hydrochloride according to claim 1, further comprising step S11 between step S1 and step S2:
The cyclization reaction is to drop the compound 2 aqueous solution into the sodium hydroxide aqueous solution, control certain temperature, react for a certain time, get the compound 4 aqueous solution after the reaction is finished, compound 4 reacts again through step S2 to get the compound 5, the total reaction formula is as follows:
3. The method for producing (S) -3-aminobutyric acid hydrochloride according to claim 2, further comprising step S111 between step S1 and step S11:
The substitution reaction comprises the steps of S11 obtaining a compound 3, adding di-tert-butyl dicarbonate into the compound 3, controlling a certain temperature, reacting for a certain time, extracting and layering after the reaction is finished, washing an organic phase by using a sodium chloride aqueous solution, and concentrating to obtain a compound 4, wherein the total reaction formula is as follows:
4. The method for producing (S) -3-aminobutyric acid hydrochloride according to claim 1, wherein the reaction solvent in step S1 is at least one of dichloromethane, tetrahydrofuran, methyltetrahydrofuran, chloroform, dichloroethane, and the like.
5. The method for producing (S) -3-aminobutyric acid hydrochloride according to claim 1, wherein the reaction temperature in step S1 is 20 to 80 ℃.
6. The method for preparing (S) -3-aminobutyric acid hydrochloride compound according to claim 1, wherein the ratio of compound 1, thionyl chloride and reaction solvent in step S1 is 1W:2.4W:8W.
7. The method for producing (S) -3-aminobutyric acid hydrochloride according to claim 2, wherein the reaction temperature in step S11 is 20 to 70 ℃.
8. The method for preparing (S) -3-aminobutyric acid hydrochloride compound according to claim 2, wherein the ratio of compound 2, sodium hydroxide and water in step S11 is 1W:1.08-3.6W:2.52W.
9. The process for producing (S) -3-aminobutyric acid hydrochloride according to claim 3, wherein the ratio of compound 3, di-tert-butyl dicarbonate and water in step S111 is 1W:3.1W:2.7W.
10. The method for producing (S) -3-aminobutyric acid hydrochloride according to claim 3, wherein the extraction solvent for the extraction and delamination in step S111 is at least one solvent selected from ethyl acetate, methylene chloride, and the like.
11. The method for producing (S) -3-aminobutyric acid hydrochloride according to claim 1, wherein the reaction solvent in step S2 is at least one of DMF, DMSO and tetrahydrofuran.
12. The method for producing (S) -3-aminobutyric acid hydrochloride according to claim 1, wherein the solvent in step S2 is 3 to 10w.
13. The method for producing (S) -3-aminobutyric acid hydrochloride according to claim 1, wherein the reaction temperature in step S2 is 20 to 80 ℃.
14. The method for producing (S) -3-aminobutyric acid hydrochloride according to claim 1, wherein the organic solvent in step S3 is at least one of ethyl acetate, 1, 4-dioxane solution, methanol, ethanol, and the like.
15. The process for producing (S) -3-aminobutyric acid hydrochloride compounds according to claim 1, wherein the organic solvent of HCl (gas) in step S3 is at least one of ethyl acetate solution of HCl (gas), 1, 4-dioxane solution of HCl (gas), methanol solution of HCl (gas) and ethanol solution of HCl (gas).
16. A (S) -3-aminobutyric acid hydrochloride compound prepared by the method for preparing a (S) -3-aminobutyric acid hydrochloride compound according to any one of claims 1 to 15.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202411481802.9A CN119775163A (en) | 2024-10-23 | 2024-10-23 | (S) -3-aminobutyric acid hydrochloride compound and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202411481802.9A CN119775163A (en) | 2024-10-23 | 2024-10-23 | (S) -3-aminobutyric acid hydrochloride compound and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN119775163A true CN119775163A (en) | 2025-04-08 |
Family
ID=95239977
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202411481802.9A Pending CN119775163A (en) | 2024-10-23 | 2024-10-23 | (S) -3-aminobutyric acid hydrochloride compound and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN119775163A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN121226189A (en) * | 2025-12-01 | 2025-12-30 | 湖南阿斯迪康药业有限公司 | A preparation process for (S)-3-aminobutyronitrile hydrochloride |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103373982A (en) * | 2012-04-20 | 2013-10-30 | 邱毅斌 | Synthetic method of 2-thiophene ethylamine |
| CN115698003A (en) * | 2020-02-07 | 2023-02-03 | 加舒布鲁姆生物公司 | Heterocyclic GLP-1 agonists |
| CN118420491A (en) * | 2024-04-25 | 2024-08-02 | 镇江中智化学科技有限公司 | Synthesis process of (S) -3-amino butyronitrile hydrochloride |
-
2024
- 2024-10-23 CN CN202411481802.9A patent/CN119775163A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103373982A (en) * | 2012-04-20 | 2013-10-30 | 邱毅斌 | Synthetic method of 2-thiophene ethylamine |
| CN115698003A (en) * | 2020-02-07 | 2023-02-03 | 加舒布鲁姆生物公司 | Heterocyclic GLP-1 agonists |
| CN118420491A (en) * | 2024-04-25 | 2024-08-02 | 镇江中智化学科技有限公司 | Synthesis process of (S) -3-amino butyronitrile hydrochloride |
Non-Patent Citations (5)
| Title |
|---|
| GARDINER, JOHN M.等: ""Synthesis of novel 1-, 1, 4- and 1, 7-substituted 2-mercapto- and 2-methylmercapto-benzimidazoles: acyclic analogs of the HIV-1 RT inhibitor, TIBO"", 《TETRAHEDRON》, vol. 51, no. 42, 16 October 1995 (1995-10-16), pages 11515 - 11530 * |
| REGISTRY: ""RN400090-62-2"", 《STNEXT》, 11 March 2002 (2002-03-11), pages 1 * |
| ROY, ARNAB等: ""Diastereoselective synthesis of a core fragment of ritonavir and lopinavir"", 《TETRAHEDRON LETTERS》, vol. 52, no. 51, 20 October 2011 (2011-10-20), pages 6968 - 6970, XP028113757, DOI: 10.1016/j.tetlet.2011.10.087 * |
| SCHAEFER, FRED C.: ""Homologs of Triethylenemelamine"", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》, vol. 77, no. 22, 1 November 1955 (1955-11-01), pages 5928 - 5930 * |
| YAMASHITA, TOHRU等: ""A Modular Synthesis of Conformationally Preorganised Extended β-Strand Peptidomimetics"", 《CHEMISTRY - A EUROPEAN JOURNAL》, vol. 21, no. 42, 17 August 2015 (2015-08-17), pages 14699 - 14702 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN121226189A (en) * | 2025-12-01 | 2025-12-30 | 湖南阿斯迪康药业有限公司 | A preparation process for (S)-3-aminobutyronitrile hydrochloride |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110590635A (en) | Preparation method of levetiracetam and intermediate thereof | |
| CN108129288B (en) | Synthesis method of trans-3-hydroxycyclobutylformic acid | |
| CN119775163A (en) | (S) -3-aminobutyric acid hydrochloride compound and preparation method thereof | |
| CN116621792A (en) | A method for preparing N-n-butyl-1,2-benzisothiazolin-3-one-1-oxide | |
| JP4162274B2 (en) | Process for producing bis (2-hydroxyphenyl-3-benzotriazole) methanes | |
| CN108467353B (en) | Preparation method of enantiopure tert-butyl sulfinamide | |
| CN108164423B (en) | Preparation method of naftifine hydrochloride | |
| CN115286504B (en) | Method for synthesizing (R) -2- (2- (tert-butoxy) -2-oxyethyl) pentanoic acid | |
| CN118496177A (en) | Method for preparing kali lazine and intermediate thereof | |
| CN117417257A (en) | A method for synthesizing amine compounds through catalytic hydrogenation | |
| CN103787858B (en) | Method for preparing 9-fluorenone through fluorene | |
| CN109369618B (en) | One-pot method for the preparation of 2-chloro-5-((2-(nitromethylene)imidazolin-1-yl)methyl)pyridine | |
| CN108409615B (en) | Method for synthesizing enantiopure tert-butyl sulfenamide | |
| CN114315755A (en) | Synthesis method of key intermediate of Tubulysin and analogues thereof | |
| CN113861167A (en) | Preparation method of Voranolan fumarate | |
| CN108727214B (en) | A kind of synthetic method of anesthetic bupivacaine impurity | |
| CN107011254B (en) | Synthesis and purification method of 2-amino-4-methylpyridine | |
| CN115925615B (en) | A method for preparing optically pure 2-methylpiperidin-5-amine | |
| CN118420569B (en) | A method for synthesizing (S)-oxetane-2-methylamine | |
| CN119504636B (en) | A method for preparing 2-(4-fluorophenyl)-6-nitro-4-(2,2,2-trifluoroethoxy)-1,2-benzothiazol-3-one, its intermediates, and applications. | |
| CN110724098A (en) | Synthetic method of 5, 7-dichloro-1, 2,3, 4-tetrahydroisoquinoline-6-carboxylic acid hydrochloride | |
| CN111100112A (en) | Benzothiophene derivative and process for producing the same | |
| CN111138333B (en) | Preparation method of (R) -2- (2, 5-difluorophenyl) -pyrrolidine | |
| CN121609644A (en) | (S) -aminonitrile hydrochloride compound and preparation method thereof | |
| CN119039158A (en) | Preparation method of aromatic amine compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |