Category: esters-buliding-blocks

34846-90-7, Adding a certain compound to certain chemical reactions, such as: 34846-90-7, name is Methyl 3-methoxyacrylate, 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 34846-90-7.

Under nitrogen protection, add 12.9g (323.5mmol) of NaH and 150g of DMF to the reaction flask at -15-10¡ãC.4-amino-1,1,1-trifluoro-3-buten-2-one50 g (359.5 mmol) solution, the system turned from colorless to light yellow and finally to a red suspension,Methyl 3-methoxyacrylate (41.75 g, 359.5 mmol) was added dropwise and reacted at this temperature for 3 hours.Concentrated hydrochloric acid was added dropwise to the reaction flask at -10¡ãC to adjust the pH of 8-9. The system changed from a deep red suspension to orange, and water was added.1.5L of dilute hydrochloric acid was used to adjust the pH to 1 to 2, and a large amount of white flocculent solids precipitated. After stirring for 0.5 hours, 81.5 g of a white product was obtained by filtration (yield, 88.3percent).The NMR analysis of the product obtained in this example is shown in Figure 1.Prove that the resulting product isN-1-methoxy-2-methoxycarbonylethyl-4,4,4-trifluoro-3-keto-1-butenamine..

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 3-methoxyacrylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Heteng Fine Chemical Co., Ltd.; Chen Sheng; Shi Guancheng; Meng Haicheng; (8 pag.)CN107628991; (2018); A;,
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3196-15-4, name is Methyl 2-bromobutyrate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 3196-15-4

1.80 g (9.66 mmol) of tert-butyl 2-(aminomethyl)azetidine-1-carboxylate [racemate] were dissolved in 25 ml of dichloromethane, 1.62 ml (1.17 g, 11.6 mmol) of triethylamine and 1.11 ml (1.75 g, 9.66 mmol) of methyl 2-bromobutanoate [racemate] were added and the mixture was stirred under reflux overnight. 1.35 ml (0.98 g, 9.66 mmol) of triethylamine and 0.89 ml (1.40 g, 7.73 mmol) of methyl 2-bromobutanoate [racemate] were then added, and the mixture was stirred under reflux overnight. After cooling to room temperature, water was added and the phases were separated. The aqueous phase was extracted twice with dichloromethane and the combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and then freed of the solvent under reduced pressure. This gave 2.64 g (83% of theory, purity: 87%) of the desired product. LC-MS (Method 6A): Rt=2.16 min (diastereomer 1, 2 isomers), Rt=2.22 min (diastereomer 2, 2 isomers); MS (ESIpos): m/z=287 [M+H]+

Statistics shows that 3196-15-4 is playing an increasingly important role. we look forward to future research findings about Methyl 2-bromobutyrate.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ALLERHEILlGEN, Swen; BUCHMUeLLER, Anja; ENGEL, Karen; GERDES, Christoph; GERICKE, Kersten Matthias; GERISCH, Michael; HEITMEIER, Stefan; HILLlSCH, Alexander; KINZEL, Tom; LIENAU, Philip; RIEDL, Bernd; ROeHRIG, Susanne; SCHMIDT, Martina Victoria; STRASSBURGER, Julia; TERSTEEGEN, Adrian; (135 pag.)US2016/108027; (2016); A1;,
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85-91-6, Adding a certain compound to certain chemical reactions, such as: 85-91-6, name is Methyl N-Methylanthranilate, 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 85-91-6.

A 500 mL three-necked flask was placed in an ice-water bath,36.21 g (0.25 mol) of calcium hypochlorite was added,Distilled water 150mL,Glacial acetic acid (36 mL),Ice water bath reaction to the solution showed light yellow,28.13 g (0.17 mol) of methyl o-methylbenzoate was slowly added,And acetone (100mL) mixture,Stir under ice-water bath for 2 hours.After completion of the reaction, 100 mL of distilled water was added,Extraction with ethyl acetate (100 mL x 4)The extracts were combined and the organic layer was washed with saturated NaHCO3 solution,Dried over anhydrous magnesium sulfate, filtered and concentrated to give 25.43 g of a dark brown liquid,No purification is required and used directly in the next step.

According to the analysis of related databases, 85-91-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Lupanshui Normal College; Yang Dan; (22 pag.)CN106279046; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 18595-18-1, name is Methyl 3-amino-4-methylbenzoate, A new synthetic method of this compound is introduced below., 18595-18-1

Method 18 4-Methyl-3-[(3-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)amino]benzoic acid A mixture of methyl 3-amino-4-methyl benzoate (1.00 g, 6.06 mmol) and 6-bromo-3-methylquinazolin-4(3H)-one (Method 1; 1.45 g, 6.06 mmol)) and KO-t-Bu (1.6 g, 15.15 mmol) in 1,4-dioxane (20 ml) was treated with Pd2(dba)3 (10% mol) and BINAP (20% mol). The reaction mixture was stirred at 80 C. for 5 h. The reaction was cooled to 25 C. and then filtered. The solid was washed with methanol-EtOAc (1:1), and collected by vacuum filtration. The resulting solid was refluxed in methanol and again filtered. The filtrate was concentrated to 40 ml. Upon cooling to 25 C., a precipitate formed which was collected by vacuum filtration. (723 mg). The product was then purified by reverse phase preparative HPLC (0.1% TFA in acetonitrile and water) to give the desired product (7%). NMR: 8.35 (s, 1H); 8.10 (s, 1H); 7.93 (s, 1H); 7.71 (m, 2H); 7.52 (m, 2H); 7.35 (d, 1H); 3.60 (s, 3H); 2.35 (s, 3H); m/z 309.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ASTRAZENECA AB; US2009/170849; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

98298-66-9,Some common heterocyclic compound, 98298-66-9, name is 1-Chloroethyl isopropyl carbonate, molecular formula is C6H11ClO3, 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 10 Preparation of 1-bromoethyl isopropyl carbonate A solution of 1-chloroethyl isopropyl carbonate (16.7 g; 0.10 mol) and hexabutylguanidinium chloride (0.43 g; 0.0011 mol) in toluene (40 ml) is heated to 115 C. and a gas stream containing 15 g (0.186 mol) of anhydrous hydrobromic acid is passed through it over 7 hours. The reaction medium is degassed with argon, the toluene is removed, the product is distilled under reduced pressure and 16.0 g of the expected product is obtained (Yld=76%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Chloroethyl isopropyl carbonate, its application will become more common.

Reference:
Patent; Societe Nationale des Poudres et Explosifs; US5202454; (1993); A;,
Ester – Wikipedia,
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The chemical industry reduces the impact on the environment during synthesis 4518-10-9, name is Methyl 3-aminobenzoate, I believe this compound will play a more active role in future production and life. 4518-10-9

(The following reaction is done in an anhydrous N2 atmosphere.) Dissolve EDC hydrochloride (122mg, 0.64mmol) and triethylamine (89muL, 0.64mmol) in anhydrous dichloromethane (3.2mL) and stir for 5min at rt. Add 2-(2,4,6-Trimethoxyphenyl)- acetic acid (14) (101mg, 0.45mmol) and DMAP (8mg, 0.06mmol) and stir for 10min. Add ethyl ester (15) (70mg, 0.42mmol) and stir the reaction solution overnight at rt. Hydrolize the reaction solution with saturated aqu. NH4Cl followed by water, separate layers, extract aqu. layer with dichloromethane (3 times) and wash the combined organic layers with water and brine and dry with Na2SO4. Remove solvent under reduced pressure. Purify crude product by preparative radial chromatography (silica gel 60PF, EtOAc/CyH 1+1) to obtain 3-[2-(2,4,6-Trimethoxy-phenyl)-acetylamino]-benzoic acid methyl ester (16) as a white solid (145mg, 95%). [K. C. Nicolaou; P. S. Baran; Y.-L. Zhong; K. Sugita; J. Am. Chem. Soc.; 2002; 124; 10; 2212-2220]. 1H NMR (400MHz, CDCl3): 3.68 (s, 2 H); 3.83 (s, 3 H); 3.84 (s, 6 H); 3.87 (s, 3 H); 6.18 (s, 2 H); 7.33 (t, 1H, J = 8.0Hz); 7.56 (br.s, 1 H); 7.69 (br.dd, 1 H, J = 7.8Hz); 7.78 (t, 1H, J = 1.8Hz); 7.90 (dd, 1 H, J1 = 8.1Hz, J2 = 1.3Hz).

The chemical industry reduces the impact on the environment during synthesis 4518-10-9. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Revotar Biopharmaceuticals AG; EP1764096; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

581065-95-4, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 581065-95-4, name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, A new synthetic method of this compound is introduced below.

00332] tert- butyl (2-(2,6-dioxopiperidin-3-yl)-l,3-dioxoisoindolin-4-yl)glycinate (0. lg, (0733) 0.25mmol) was dissolved in lmL TFA. The mixture was stirred at room temperature for 2 hours, then concentrated under reduced pressure to afford solid product which was used in the following reaction without further purification. (2-(2,6-dioxopiperidin~3~yl)-i ,3- dioxoisoindoim-4-yl)giycme product (0.05g, 0.15mmol) was mixed with HATU (0. i l4g, 0.3mrnol) in 3mL DMF. EtsN (0.105mL, 0.75mmol) was added. The mixture was stirred for lOmins before the amino-PEG4-/~Butyl ester (0.05g, 0.15mmo) was added. The reaction was then stirred at room temperature overnight. The solution was next subjected to preparative HPLC purification to afford 48mg product (51%). LCMS (ESI) m/z 579.32 (0734) (show as free acid instead of /-butyl ester) [(M+H)+; calcd for CsoHisNiOiC; 635.29]

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BUHRLAGE, Sara; ANDERSON, Kenneth C.; HIDESHIMA, Teru; GRAY, Nathanael S.; LIU, Xiaoxi; (137 pag.)WO2019/118728; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 349-43-9, name is Ethyl 2-fluoropropionate, 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 349-43-9, 349-43-9

Add 12.0 g (0.1 mol) to a 250 ml four-necked flask with a condenserEthyl 2-fluoropropionate,240g of carbon tetrachloride,24.0 g (0.15 mol) of bromine,20.2 g (0.15 mol) of sulfuryl chloride,0.6g azoisobutyronitrile,StirThe reaction was carried out by heating to 70 ¡ãC.After 10 h, the conversion of methyl 2-fluoropropionate was 98.2percent.The selectivity to ethyl 2-fluoro-2-bromopropionate was 88.4percent.

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, Ethyl 2-fluoropropionate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Juhua Group Technology Center; Ye Lifeng; Wang Shuhua; (5 pag.)CN104892409; (2018); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 541-16-2 as follows. 541-16-2

General procedure: alpha,beta-Unsaturated aldehyde (3.0 mmol) and malonate (3.0 mmol) were added into asolution of TiCl4 (6.0 mmol) in CCl4 (2.0 mL) and THF (10 mL) at 0 C, Then, pyridine (0.96 mL, 12.0 mmol) in THF (2 mL) was added dropwisely over 1 h. The resulting mixture was stirred at room temperature overnight. After quenched with water, the mixture was extracted with ethyl acetate, dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography with hexane/ethyl acetate = 20/1 to afford the product.

According to the analysis of related databases, 541-16-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wei, Xu; Lu, Junzhu; Duan, Wei-Liang; Synthesis; vol. 48; 23; (2016); p. 4155 – 4160;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

87-13-8, Name is Diethyl 2-(ethoxymethylene)malonate, 87-13-8, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

A mixture of aniline (25.6 g, 0.28 mol) and diethyl 2-(ethoxymethylene)malonate (62.4 g, 0.29 mol) was heated at 140-150 C. for 2 h. The mixture was cooled to room temperature and dried under reduced pressure to afford 2-phenylaminomethylene-malonic acid diethyl ester as a solid, which was used in the next step without further purification. 1H NMR (d-DMSO) delta 11.00 (d, 1H), 8.54 (d, J=13.6 Hz, 1H), 7.36-7.39 (m, 2H), 7.13-7.17 (m, 3H), 4.17-4.33 (m, 4H), 1.18-1.40 (m, 6H).

Statistics shows that Diethyl 2-(ethoxymethylene)malonate is playing an increasingly important role. we look forward to future research findings about 87-13-8.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; US2012/309758; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics