Esters-buliding-blocks

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. 3153-37-5, name is Methyl 4-chlorobutyrate, A new synthetic method of this compound is introduced below., COA of Formula: C5H9ClO2

EXAMPLE 1 Methods for the preparation of the compounds of the invention are disclosed in U.S. Pat. No. 6,147,250. The following is a method of producing Compound A. Probucol (5, 9.69 mmol) and methyl 4-chlorobutyrate (3.1 g. 1.4 eq) were stirred in DMF (15 mL) and potassium fluoride on alumina (7 g, 5 eq) was added. The mixture was stirred at room temperature under nitrogen for 20.5 hours. It was filtered, diluted with ethyl acetate (100 mL), washed with water and brine, dried over sodium sulfate, and evaporated. Chromatography (MPLC, 10% to 80% of dichloromethane in hexanes) gave 0.98 g of methyl 4-[4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenoxy]butyrate. Methyl 4-[4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenoxy]butyrate (0.95 g, obtained above) was dissolved in THI/MeOH/H2O (4:1;1, 15.4 mL) and lithium hydroxide hydrate (0.19 g) was added. The mixture was stirred at room temperature for four hours and then acidified with 0.3 N HCl. The mixture was poured into brine and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and evaporated to give 0.60 g of 4-[4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenoxy]butyric acid (Compound A) as a solid.

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; Edwards, David B.; Somers, Patricia K.; Glass, Mitchell; US2002/156022; (2002); A1;,
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 13671-00-6 as follows. Safety of Methyl 2,6-difluorobenzoate

Example 43A 2,6-Difluorophenyl)(2H2)methanol At 0 C., 1.00 g (5.81 mmol) of methyl 2,6-difluorobenzoate were initially charged in 20 ml of THF, and 11.62 ml of (11.62 mmol) of lithium aluminium deuteride [=LiAlD4=lithium tetrahydrido(2H4)aluminate](1 M solution in THF) were added dropwise. The mixture was stirred for 1 h in an ice bath that slowly thawed. 0.58 ml of water, 0.58 ml of 2 N aqueous sodium hydroxide solution and 1.16 ml of water were then added in succession to the reaction solution. The precipitate formed was filtered off and washed thoroughly with THF. The filtrate was concentrated and the residue was dried under high vacuum. This gave 0.743 g of the product (88% of theory, purity about 90%), which was reacted further without purification. LC-MS (Method 14): Rt=2.38 min MS (EIpos): m/z=146 (M)+ 1H NMR (400 MHz, DMSO-d6): delta=5.20 (s, 1H), 7.08 (t, 2H), 7.39 (quint, 1H).

According to the analysis of related databases, 13671-00-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; HARTUNG, Ingo; FOLLMANN, Markus; JAUTELAT, Rolf; STRAUB, Alexander; HAssFELD, Jorma; LINDNER, Niels; SCHNEIDER, Dirk; WUNDER, Frank; STASCH, Johannes-Peter; REDLICH, Gorden; LI, Volkhart Min-Jian; BECKER-PELSTER, Eva Maria; KNORR, Andreas; US2014/128386; (2014); A1;,
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. 1186-73-8, name is Trimethyl methanetricarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Trimethyl methanetricarboxylate

A mixture of N-benzyl-2-(3,6-dihydro-2H-pyran-4-yl)-7-isopropyl-3-(3-methoxypropoxy)-7,8-dihydrooxepino[3,2-b]pyridin-9(6H)-imine (600 mg, 1.29 mmol), trimethylmethanetricarboxylate (491 mg, 2.58 mmol) in Ph20 (3 mL) was degassed under vacuum and purged with nitrogen gas (cycle repeated 3 times). The mixture was stirred at 220 C for 15 min under nitrogen atmosphere. The mixture was cooled to rt and purified directly by normal phase S1O2 chromatography (0-50% EtO Ac/petroleum ether) to give methyl 11-benzyl-2-(3,6-dihydro-2H-pyran-4-yl)-8-hydroxy-7-isopropyl-3-(3-methoxypropoxy)-10-oxo-6,7,10,11-tetrahydrooxepino[3,2-b:4,5-b’]dipyridine-9-carboxylate as a yellow oil (430 mg, 56% yield, m/z: 591 [M+H] observed).

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; ARBUTUS BIOPHARMA, INC.; CHEN, Shuai; DORSEY, Bruce D.; FAN, Yi; GOTCHEV, Dimitar B.; QUINTERO, Jorge; (252 pag.)WO2019/177937; (2019); A1;,
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. 1130165-74-0, name is Ethyl 4-bromo-3-fluorobenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 1130165-74-0

Preparation Example 20 A mixture of ethyl 4-bromo-3-fluorobenzoate (1 g), cyclopropylboronic acid monohydrate (643 mg), tetrakistriphenylphosphinepalladium (235 mg), potassium phosphate (3.1 g), toluene (10 ml), and water (1 ml) was thoroughly stirred at 110 C. overnight. To the reaction mixture was added water, followed by carrying out a separation of the layers using ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was crudely purified by silica gel column chromatography (hexane:ethyl acetate=85:15), and then to a mixture of the crude product, THF (20 ml), and MeOH (20 ml) was added a 1 M aqueous sodium hydroxide solution (20 ml), followed by stirring at room temperature overnight. To the reaction mixture was added 1 M hydrochloric acid (20 ml), followed by concentrating under reduced pressure to remove the organic solvent. The precipitated solid was collected by filtration to obtain 600 mg of 4-cyclopropyl-3-fluorobenzoic acid as a colorless solid.

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; ASTELLAS PHARMA INC.; US2012/46292; (2012); A1;,
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. 14064-10-9, name is Diethyl 2-chloromalonate, A new synthetic method of this compound is introduced below., Computed Properties of C7H11ClO4

DBU (4.64 g, 30.5 mmol) was added at room temperature to a solution of 8 (7.00 g, 27.7 mmol) and diethyl chloromalonate (6.47 g, 33.2 mmol) in DMF (70 ml). After stirring at this temperature for 24 h, the reaction mixture was quenched with H2O (200 ml) at 0 ¡ãC. The aqueous layer was extracted with AcOEt (200 ml ¡Á 2). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane-AcOEt) to give 9 (4.67 g, 50percent) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta 1.38 (3H, t, J = 7.1 Hz), 1.47 (9H, s), 1.87-1.95 (2H, m), 2.38-2.49 (1H, m), 2.74-2.87 (2H, m), 4.10-4.28 (2H, m), 4.35 (2H, q, J = 7.1 Hz), 4.50 (2H, br s), 7.06 (1H, s).

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:
Article; Koshizawa, Tomoaki; Morimoto, Toshiharu; Watanabe, Gen; Watanabe, Toshiaki; Yamasaki, Nao; Sawada, Yoshikazu; Fukuda, Tomoaki; Okuda, Ayumu; Shibuya, Kimiyuki; Ohgiya, Tadaaki; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3249 – 3253;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 2555-28-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2555-28-4, name is 7-Methoxy-4-methylcoumarin belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 4-Methyl-6,7-dimethoxycoumarin (0.05 g, 0.227 mmol) was dissolved in acetonitrile (5 ml) in a microwave vessel. N-Bromosuccinimide (0.06 g, 0.340 mmol) was added to the mixture and the vessel inserted into the microwave at 250 W for 5 min at 80 C. The reaction was monitored by thin layer chromatography (silica gel, 3:1 CH2Cl2/EtOAc). Upon completion, the reaction mixture was cooled and the resultant precipitate was collected by vacuum filtration. The crude product was then recrystallized from a mixture of CH2Cl2/MeOH to yield 3-bromo-4-methyl-6,7-dimethoxycoumarin (1a, 0.060 g, 89%)

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, 7-Methoxy-4-methylcoumarin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Marriott, Karla-Sue C.; Bartee, Rena; Morrison, Andrew Z.; Stewart, Leonard; Wesby, Julian; Tetrahedron Letters; vol. 53; 26; (2012); p. 3319 – 3321;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

110661-91-1, name is tert-Butyl 4-bromobutanoate, 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. Recommanded Product: tert-Butyl 4-bromobutanoate

Intermediate 6 (10.47 g, 11.73 mmol) was dissolved in acetonitrile (500 ml) and tert-butyl bromoacetate (10.0 g, 44.84 mmol) and DIPEA (9.08 mg, 70.38 mmol) were added. The reaction mixture was stirred at RT for 14 days and then filtered. Evaporation of the solvent gave crude product which was purified using a Combiflash companion (120 g cartridge) eluting with 0-10% MeOH in DCM. The solid product was triturated with Et2O to give a white solid. Yield: 8.79 g (72%) LC-MS (Method 2): Rt = 2.93 min, m/z = 1036 [M+H]+

The synthetic route of 110661-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARGENTA DISCOVERY LIMITED; WO2009/60206; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 5445-17-0, 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. 5445-17-0 name is Methyl 2-bromopropanoate, 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.

Example 22; Preparation of the Compound E-13; Preparation of ethyl 2-methyl-2-(2-methyl-4-(1-(3-(4-methyl-5-oxo-1-(4-trifluoromethyl-phenyl)-4,5-dihydrogen-1H-1,2,4-triazolyl))-benzylthio)-phenoxy)-acetate(E-13); In a 250 ml three-necked flask, to a stirred mixture of lithium aluminum tetrahydride (LiAlH4, 1.0 g, 26.4 mmol) and tetrahydrofuran (THF 30 ml) was added dropwise a solution of 3-methyl-4-hydroxy-phenyl thiocyanic acid (1.38 g, 8.35 mmol) in 20 ml of tetrahydrofuran at 0 C. After 30 min of stirring at 0 C., the mixture was allowed to warm up to room temperature and then stirred for another 2 hours at room temperature. The reaction was quenched by adding ethanol (10 ml). The value of pH of the mixture was adjusted to pH 3-4 by adding 6 N hydrochloric acid in an ice water bath, and then the aqueous phase was extracted with ethyl acetate (3¡Á80 ml). The combined organic layer was dried over anhydrous magnesium sulfate, filtrated, concentrated under reduced pressure, and purified by column chromatography (silica-gel H: 300-400 mesh; petroleum ether/ethyl acetate=5:1 v/v) to yield 1.44 g of a disulfide (yellow jelly-like liquid, yield: 62%).Its structure was characterized by the following data from nuclear magnetic resonance spectroscopy and Mass spectroscopy:1H NMR (400 MHz, CDCl3) delta 2.2 (s, 3H), 5.35 (s, 1H), 6.69 (d, J=8.28 Hz, 1H), 7.18 (dd, J=8.23 Hz, 2.23 Hz, 1H), 7.24 (d, J=2.24 Hz, 1H); 13C NMR (100 MHz, CDCl3) delta 15.7, 115.5, 125.0, 128.3, 130.2, 134.0, 154.4; MS (ESI) m/z 278.33 (M+H)+.In 250 ml single-necked flask, to a stirred solution of above crude product (0.7 g, 2.59 mmol) in acetonitrile (60 ml) were added methyl 2-bromo-propionate (0.7 ml, 6.0 mmol) and potassium carbonate (K2CO3, 2 g, 14.5 mmol). The resulting mixture was stirred at room temperature overnight. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (100 ml), and filtrated. The combined solution was evaporated under reduced pressure to give a residue which was purified by chromatography (silica-gel H: 300-400 mesh; petroleum ether/ethyl acetate=5:1 v/v) to yield 1.0 g of a yellow jelly-like liquid (yield: 86%).Its structure was characterized by the following data from nuclear magnetic resonance spectroscopy:1H NMR (400 MHz, CDCl3) delta 1.63 (d, J=6.84 Hz, 1H); 2.34 (s, 3H), 3.75 (s, 3H), 4.73 (q, J=6.84 Hz, 1H), 6.57-6.61 (m, 1H), 7.19-7.27 (m, 2H).In a 250 ml single-necked flask, to a stirred solution of the above-described product (1.0 g, 2.22 mmol) in ethanol (15 ml) were added 15 ml of water and 5 ml of concentrated hydrochloric acid. Zinc powder (10 g, 153 mmol) was added slowly. After the addition, the reaction mixture was stirred at room temperature for 30 min and then extracted with dichloromethane (3¡Á50 ml). The organic phases were combined, dried over anhydrous magnesium sulfate, filtrated, and concentrated under reduced pressure to yield a pale-yellow liquid.In a 150 ml single-necked flask, to a stirred solution of the above crude product in 30 ml of acetonitrile were added a solution of 341-bromo-benzyl)-4-methyl-1-(4-trifluoromethyl)phenyl-1H-1,2,4-triazole-5(4H)-one (III-1) (1.8 g, 4.36 mmol) in acetonitrile (30 ml) and potassium carbonate (K2CO3, 2.5 g, 18.1 mmol). The reaction mixture was stirred at room temperature for 6 hours. After the reaction was completed, the reaction mixture was diluted by adding 100 ml of ethyl acetate, filtrated, concentrated under reduced pressure, and subjected to column chromatography (silica-gel H: 300-400 mesh; petroleum ether/ethyl acetate=5:1 v/v) to yield 1.2 g E-13 (a pair of diastereoisomers) (a pale-yellow jelly-like liquid, yield: 50%).Its structure was characterized by the following data from nuclear magnetic resonance spectroscopy:1H NMR (400 MHz, CDCl3) delta 1.61 (d, J=6.84 Hz, 1H); 2.18 (s, 3H), 3.15 (s, 3H), 3.70 (d, J=12.61 Hz, 3H); 4.70 (q, J=6.82 Hz, 1H); 5.18 (s, 1H); 6.51 (d, J=8.46 Hz, 1H), 7.0-7.11 (m, 1H), 7.10-7.15 (m, 1H), 7.34-7.37 (m, 5H), 7.67 (d, J=8.74 Hz, 2H), 8.11 (d, J=8.74 Hz, 2H); 13C NMR (100 MHz, CDCl3) delta 16.1, 18.5, 28.1, 50.6, 52.2, 72.7, 112.1, 118.2, 123.0, 125.5, 126.2, 126.8, 127.1, 128.2, 128.5, 128.9, 133.8, 135.2, 137.7, 140.6, 146.5, 152.6, 156.9, 172.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-bromopropanoate, and friends who are interested can also refer to it.

Reference:
Patent; Zhejiang Hisun Pharmaceutical Co., Ltd.; US2011/319458; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 73792-08-2, name is Methyl 4-amino-2-fluorobenzoate, 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 73792-08-2, name: Methyl 4-amino-2-fluorobenzoate

Add 2-fluoro-4-aminobenzoic acid methyl ester 2 (3.70 g, 21.8 mmol), cyclobutanone (2.44 g, 34.8 mmol), potassium cyanide (2.12 g, 32.6 mmol) and 37 mL to a 250 mL two-necked flask. Acetic acid, the temperature was raised to 80 C for 12 h, TLC monitoring reaction, (petroleum ether: ethyl acetate = 20:3), after the reaction was completed, 20 mL of water was added to the reaction solution, ethyl acetate extraction (30 ¡Á 3 mL), decompression In addition to the solvent, Compound 3, 5.01 g, brown red solid, yield: 92.5%.

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; Changsha Zeda Pharmaceutical Technology Co., Ltd.; Chen Yongheng; Xu Guangyu; Zhou Wenqiang; (23 pag.)CN108976171; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 2905-65-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2905-65-9, name is Methyl 3-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Substituted benzoic acid (1.0 mmol) was dissolved in thionylchloride and refluxed for 2 h, then the solvent was removed underreduced pressure to obtain the white solid. The white solid in methanol was added concentrated sulfuric acid (1 mL) and themixture was refluxed for 4 h, the solvent was removed to obtaincrude solid. The crude solid was extracted with ethyl acetate andwater. The solvents were evaporated to afford the pure product.Finally, the pure product was dissolved in ethanol, and the hydrazinehydrate was added. The mixture was refluxed for 9 h, and thesolvent was removed

The synthetic route of Methyl 3-chlorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lian, Zhi-Min; Sun, Juan; Zhu, Hai-Liang; Journal of Molecular Structure; vol. 1117; (2016); p. 8 – 16;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics