Category: 29006-01-7

Some common heterocyclic compound, 29006-01-7, name is Methyl 4-methoxybutanoate, molecular formula is C6H12O3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 29006-01-7

The toluenic solution obtained in A) (4.00 Kg of 4-trifluoromethylbenzylamine) was charged in a reactor. After distillation until an oil residue was obtained, 3.20 Kg of methyl 4-methoxybutyrate, 0.40 kg of 30% sodium methylate were added. The solution was then heated to 1 10-1200C, distilling at atmospheric pressure in order to remove all methanol (also methanol freeing from the reaction) and maintaining such temperature for at lest two hours. The reactor at 1 10-120C was then put under vacuum for at least one hour. At the end of the reaction, 12.0 Kg of toluene, 2.0 Kg of water and 0.40 Kg of 80% acetic acid were added to the mass. After stirring, the lower aqueous phase was separated and removed. The organic phase was then distilled under vacuum to a oil residue. To such a residue, 4.00 Kg of ethylacetate, 12.0 Kg of n-hexane were added and the final mass was heated to 40-60 C until a complete solution was obtained. Then the solution was brought to 20-30 C and so maintained until a good precipitation was obtained. The mass was then cooled to 0C – 10C, centrifuged by washing with a mixture of 0.80 Kg of ethylacetate, 4.00 Kg of n-hexane. The obtained humid product was used as such in the following step.About 3.8 Kg of crude N-[4-(trifluoromethyl)benzyl]-4-methoxybutyramide were obtained. Yield: 60.5%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 29006-01-7, its application will become more common.

Reference:
Patent; LABORATORIO FARMACEUTICO C.T. S.R.L.; WO2009/62949; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 29006-01-7, name is Methyl 4-methoxybutanoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 29006-01-7, Computed Properties of C6H12O3

To a stirred, cooled (-78 C.) solution of 1.32 g (10.0 mmol) of methyl 4-methoxybutanoate in 15 mL of anhydrous THF under an atmosphere of nitrogen was added 10.5 mL (10.5 mmol) of a 1.0 M solution of LiHMDS in tetrahydrofuran. The resulting mixture was stirred for 1 h, then 1.09 g (10 mmol) of chlorotrimethylsilane was added. After stirring for 20 min, 1.78 g (10.0 mmol) of solid N-bromosuccinimide was added and the mixture was stirred for 2 h at -78 C., then slowly warmed to ambient temperature over 40 min. The reaction was quenched with a saturated aqueous ammonium chloride solution and then the aqueous phase was extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated to dryness in vacuo. The crude residue was dissolved in 15 mL of DMF and 5.5 g (40 mmol) of potassium carbonate followed by 3.4 g (50 mmol) of 1H-pyrazole were added. The resulting mixture was heated to 80 C. for 40 min, then cooled to ambient temperature. The reaction was diluted with 75 mL of water and extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness in vacuo. The crude residue was purified by reverse phase HPLC (TMC Pro-Pac C18; 0-75% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient) to yield the title compound (0.26 g, 13%). LC-MS: m/z (ES) 199 (MH)+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Berger, Richard; Chang, Lehua; Edmondson, Scott D.; Goble, Stephen D.; Ha, Sookhee Nicole; Kar, Nam Fung; Kopka, Ihor E.; Li, Bing; Morriello, Gregori J.; Moyes, Chris R.; Shen, Dong-Ming; Wang, Liping; Zhu, Cheng; US2009/253705; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 29006-01-7, The chemical industry reduces the impact on the environment during synthesis 29006-01-7, name is Methyl 4-methoxybutanoate, I believe this compound will play a more active role in future production and life.

Step 1. 4-Methoxybutanal [00207] To a solution of methyl 4-methoxybutanoate (3.43 g, 26 mmol) in DCM (26 mL) was added DIBAL-H (33 mL, 33 mmol, 1 M in toluene) at -78 C. After stirring at -78 C for 50 mins, the reaction was quenched with MeOH (10 mL) and then brine (20 mL). The separated organic layer was dried over Na2S04, concentrated in vacuo to give 4-methoxybutanal (2.25 g, 85%) as colorless liquid, which was used in the next reaction without further purification.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 4-methoxybutanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK PATENT GMBH; KARRA, Srinivasa R.; GOUTOPOULOS, Andreas; (137 pag.)WO2016/19228; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 29006-01-7, name is Methyl 4-methoxybutanoate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 4-methoxybutanoate

Description 374-Methoxybutanoic acid (P37)To a solution of methyl 4-methoxybutanoate (555.6 mg) in THF (6 mL), sodium hydroxide (6.31 mL) (2M aqueous solution) was added, the reaction mixture was stirred overnight. Most solvent was removed by rotavap, diluted with water (5 mL), washed with DCM (5 mL). The aqueous layer was acidified with 3 M HC1 (aq.) to pH 2, extracted with EtOAc twice (2x 15 mL). The combined organic layer was dried over Na2504 and filtered. The filtrate was concentrated to afford the titlecompound (491.3 mg) as colorless oil. 111 NMR (400 MHz, DMSO-d6): 12.02 (s, 1H), 3.30 (t, J=6.6 Hz, 2H), 3.21 (s, 3H), 2.23 (t, J= 7.3 Hz, 2H), 1.71 (quin, J= 6.9 Hz, 2H).

According to the analysis of related databases, 29006-01-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; DENG, Jing; LEI, Hui; MA, Xin; LIN, Xichen; WO2015/180612; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 29006-01-7,Some common heterocyclic compound, 29006-01-7, name is Methyl 4-methoxybutanoate, molecular formula is C6H12O3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step A: A solution of methyl 4-methoxybutanoate (1.48 g, 1.0 equiv) in methanol was treated with LiOH.H2O (3.1 equiv), and the mixture was heated to 50 C. for 3 hours. The mixture was cooled to ambient temperature and 5.0 N HCl (7.0 mL) was added. The mixture was concentrated to dryness under reduced pressure, CH2Cl2 was added and the mixture sonicated for 30 minutes. The insoluble salts were removed by vacuum filtration and the filtrate concentrated to afford 4-methoxybutanoic acid as a colorless oil (1.023 g, 77%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-methoxybutanoate, its application will become more common.

Reference:
Patent; Miknis, Greg; Lyssikatos, Joseph P.; Laird, Ellen; Tarlton, Eugene; Buckmelter, Alexandre J.; Ren, Li; Rast, Bryson; Schlacter, Stephen T.; Wenglowsky, Steven Mark; US2007/49603; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 29006-01-7, name is Methyl 4-methoxybutanoate, molecular formula is C6H12O3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of Methyl 4-methoxybutanoate

The toluenic solution obtained in A) (4.00 Kg of 4-trifluoromethylbenzylamine) was charged in a reactor. After distillation until an oil residue was obtained, 3.20 Kg of methyl 4-methoxybutyrate, 0.40 kg of 30% sodium methylate were added. The solution was then heated to 1 10-1200C, distilling at atmospheric pressure in order to remove all methanol (also methanol freeing from the reaction) and maintaining such temperature for at lest two hours. The reactor at 1 10-120C was then put under vacuum for at least one hour. At the end of the reaction, 12.0 Kg of toluene, 2.0 Kg of water and 0.40 Kg of 80% acetic acid were added to the mass. After stirring, the lower aqueous phase was separated and removed. The organic phase was then distilled under vacuum to a oil residue. To such a residue, 4.00 Kg of ethylacetate, 12.0 Kg of n-hexane were added and the final mass was heated to 40-60 C until a complete solution was obtained. Then the solution was brought to 20-30 C and so maintained until a good precipitation was obtained. The mass was then cooled to 0C – 10C, centrifuged by washing with a mixture of 0.80 Kg of ethylacetate, 4.00 Kg of n-hexane. The obtained humid product was used as such in the following step.About 3.8 Kg of crude N-[4-(trifluoromethyl)benzyl]-4-methoxybutyramide were obtained. Yield: 60.5%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 29006-01-7, its application will become more common.

Reference:
Patent; LABORATORIO FARMACEUTICO C.T. S.R.L.; WO2009/62949; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 29006-01-7, name is Methyl 4-methoxybutanoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 29006-01-7, Quality Control of Methyl 4-methoxybutanoate

26 6-Bromo-3-(3-methoxypropyl)-[1,2,4]triazolo[4,3-a]pyridine; A mixture of 18. 80 g of (5-bromopyridin-2-yl) hydrazine (77992-44-0] and 14. 54 g of methyl 4-methoxybutyrate [29006-01-7] is heated to reflux over 16 hours. The reaction solution is subsequently cooled and purified by means of flash chromatography (SiO2 60F). The title compound is identified on the basis of the Rf value

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; SPEEDEL EXPERIMENTA AG; WO2005/90304; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 29006-01-7,Some common heterocyclic compound, 29006-01-7, name is Methyl 4-methoxybutanoate, molecular formula is C6H12O3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 1 Preparation of the compound of formula (I) (referred as ACGET61 ) Formula (I) In a round-bottomed flask equipped with an efficient condenser and a magnetic stirrer, Ri (MW: 175.088; 4.43g) and R2 (MW:132.16; 3.347g) are added in an 1 :1 molar ratio. NH4CI (443mg) is then added as catalyst (10% by weight with respect to Ri). The mixture is heated at 150C for 45h and it assumes a deep green / dark purple colour. The disappearance of the reagent is monitored by TLC (AcOEt: Hexane 1 :2) using ninhydrin as detecting agent (prepared dissolving 200mg ninhydrin in 150 ml EtOH). When the reagent is completely disappeared, the reaction mixture is cooled and the residue is dissolved in DCM, washed three times with HCI 3N then with water till neutral pH. The crude product thus obtained is purified by column chromatography eluting with a gradient of AcOEt: Hexane (from 1 : 10 to 1 :1 ). The pure product (ACGET61 , MW 275.1 1 ) is obtained as a white / light pink solid in 64% yield.

The synthetic route of 29006-01-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LABORATORIO FARMACEUTICO C.T. S.R.L.; CACCIAGLIA, Roberto; LOCHE, Antonella; (33 pag.)WO2017/21438; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 29006-01-7,Some common heterocyclic compound, 29006-01-7, name is Methyl 4-methoxybutanoate, molecular formula is C6H12O3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Lithium diisopropylamide was prepared by addition of n-butyllithium (2.5 M in hexanes, 11.7 mL, 58.8 mmol) to diisopropylamine (9.7 mL, 70.6 mmol) in dry tetrahydrofuran (100 mL) at -78 C. Stirring was continued for 15 min at -78 C before methyl 4-methoxybutanoate (6.84 g, 51.8 mmol) was added to the reaction mixture. Stirring was continued for 20 min at -78C and benzaldehyde (5g, 47.1 mmol) in tetrahydrofuran (20 mL) was added, and the reaction mixture allowed to warm slowly to room temperature. Stirring was continued for 2 hours, water (50 mL) was added under stirring and the mixture was extracted with ether (3 x 50 mL). The combined organic extracts were washed with brine, dried with sodium sulfate, filtered and evaporated under reduced pressure to afford methyl 2-(hydroxy(phenyl)methyl)-4-methoxybutanoate (10.7 g, 44.9 mmol) in 95% yield. LCMS (ESI+): 261.1 (M+Na).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-methoxybutanoate, its application will become more common.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; AUDIA, James, Edmund; COTE, Alexandre; DUPLESSIS, Martin; GEHLING, Victor, S.; HARMANGE, Jean-christophe; VASWANI, Rishi, G.; (274 pag.)WO2016/172496; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 29006-01-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 29006-01-7 name is Methyl 4-methoxybutanoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Methyl 4-methoxybutyrate 1a (1.6 g, 12.1 mmol) was added to 50 mL of tetrahydrofuran, and the temperature was lowered to -78 C.using a dry ice-acetone bath. Lithium bis-trimethylsilylamide (12.7mL) was addedslowly. 12.7 mmol). After completion of the addition, the reaction was stirred for 1 hour.Trimethylchlorosilane (1.31 g, 12.1 mmol) was added. The reaction was continued for 20 minutes with the addition of N-bromosuccinimide(2.15 g, 12.1 mmol). ), The reaction was stirred for 2 hours.The dry ice-acetone bath was removed, the temperature of the reaction solution was naturally raised to room temperature, thereaction was quenchedwith saturatedammonium chloride solution, the reaction solution was extracted with ethyl acetate (50 mL×3), the organic phases were combined, and the organic phases were separately used with water(50 mL). It was washed with sodium chloride solution (50 mL), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure.The resulting residue was purifiedby silica gel column chromatographyusing eluent system B to give the title product 1b (900 mg, colorless oil).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-methoxybutanoate, and friends who are interested can also refer to it.

Reference:
Patent; Jiangsu Hengrui Pharmaceutical Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; Yang Fanglong; Chi Jiangtao; He Feng; Tao Weikang; (33 pag.)CN107793396; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics