Category: 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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C9H16O3

Tert-butyl(chloro)diphenylsilane (18 ml, 68 mmol, GAS No 58479-61 -1) was added drop wise to a mixture of ethyl 4-hydroxycyclohexanecarboxylate (9.4 ml, 57 mmol, GAS No 17159-80-7), 1H-imidazole (9.68 g, 142 mmol, GAS No 16681 -56-4) and N,N-dimethylpyridin-4-amine (348 mg, 2.85 mmol, GAS No 1122-58-3) in DMF (81 ml), and the mixture was stirred at roomtemperature for 24 h. For work-up, the mixture was poured into water, extracted with ethyl acetate (3x) and the combined organic phases were washed until pH=7 as reached. The organic phase was dried over sodium sulfate and was concentrated under reduced pressure. The residue was purified by flash chromatography (340 g SNAP cartridge, hexane/ethyl acetate gradient, 5percent -> 30percent ethyl acetate) to give the title compound (21 g).

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; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHGRABER, Philipp; WAGNER, Sarah; SUeLZLE, Detlev; BENDER, Eckhard; LI, Volkhart, Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; (232 pag.)WO2018/78009; (2018); A1;,
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Application of 27492-84-8, 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. 27492-84-8 name is Methyl 4-amino-2-methoxybenzoate, 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.

To a solution of methyl 4-amino-2-methoxybenzoate (2.0 g, 0.0 11 mol) in DCM (50 mL) cooled to 0 C was added triethylamine (3.0 mL, 0.022 mol) and the reaction mixture was stirred for 10 minutes. Acetyl chloride (1.3 g, 0.0 165 mol) was addeddropwise and the reaction was stirred for 3 h. Water (50 mL) was added and the aqueous layer was extracted with DCM (2 x 50 mL). The combined organic extracts were dried over sodium sulfate, filtered and volatiles were evaporated to dryness under reduced pressure to give methyl 4-acetamido-2-methoxybenzoate (2.3 g, 0.01 mol, 91% yield) as a light brown solid. ?H NMR (400 MHz, DMSO-d6) oe 10.22 (s,1H), 7.66 (d, J= 8.8 Hz, 1H), 7.47 (d, J= 1.6 Hz, 1H), 7.20 (dd, J 8.4, 2.0 Hz, 1H),3.74-3.79 (m, 6H), 2.07 (s, 3H); LCMS (ESI) m/e 224.2 [(M+H), calcd for C11H14NO4, 224.08]; LC/MS retention time (method B): ti = 1.20 mm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-amino-2-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARTZ, Richard A.; AHUJA, Vijay T.; MACOR, John E.; BRONSON, Joanne J.; DASGUPTA, Bireshwar; DZIERBA, Carolyn Diane; NARA, Susheel Jethanand; KARATHOLUVHU, Maheswaran Sivasamban; (226 pag.)WO2016/53794; (2016); A1;,
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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. 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, A new synthetic method of this compound is introduced below., SDS of cas: 816-27-3

2-(2-fluorophenyl)acetohydrazide (7.05 g, 41.9 mmol) was partially dissolved in ethanol (30 mL), and then ethyl 2-ethoxy-2-iminoacetate (6.39 g, 44.0 mmol) and diethyl ether (35 mL) were added. The reaction mixture was stirred for 0.5 hours, and diethyl ether (100 mL) was added. The resulting mixture was stirred for 18 hours. The solid was filtered off, rinsed with diethyl ether, and dried to give ethyl 2-amino-2-(2-(2-(2- fluorophenyl)acetyl)hydrazono)acetate as an off-white solid (10 g, 89% yield). MS ES+ m/z 26% [M+H]+; NMR (400 MHz, DMSO-de) delta 9.80-10.25 (m, 1H), 7.25-7.43 (m, 2H), 7.09-7.21 (m, 2H), 6.42-6.60 (m, 2H), 4.23 (dq, J=1.52, 7.07 Hz, 2H), 3.92 (s, 1H), 3.58 (s, 1H), 1.26 (dt, J=5.05, 7.07 Hz, 3H).

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ANBARI, Jill Marinis; BERTIN, John J.; JEONG, Jae U.; (139 pag.)WO2018/154520; (2018); 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. 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H8BrNO2

Example 40 theta-Cyano^’-methoxy-biphenyl-S-carboxylic acid methyl esterStep 1Step 1 : Methyl 4-amino-3-bromo benzoate (0.5 g, 2.17 mmol) was dissolved in dry dichloromethane (5 ml.) and the solution was cooled to -100C. A solution of BF3-Et2O (0.41 ml, 3.26 mmol) followed by te/f-butyl nitrite (0.32 mL, 2.72 mmol) was added dropwise to the mixture. The very dense solution was allowed to reach room temperature and was then diluted with hexanes (10 mL). The resulting solid was collected by filtration and washed again with hexanes. This was rapidly transferred in a flask containing a solution of NaCN (0.32 g, 6.52 mmol) and CuCN (0.233g, 2.61 mmol) in H2O/toluene (2:1 ; 3 mL) at 5C and stirred at this temperature for 30 min.. The mixture was then allowed to reach room temperature and finally it was heated at 600C for a further 25 min. The solution was then cooled to room temperature and then partitioned between water (15 mL) and EtOAc (15 mL). The organic phase was washed with brine, dried (Na2SO4) a nd solvent was rem oved in vacuo. Recrystallisation from hexanes/EtOAc gave 3-bromo-4-cyano-benzoic acid methylester as a grey solid (0.213g, 41 %). 1H NMR (400 MHz, c/6-Acetone): 8.35 (1 H, d), 8.17 (1 H, dd), 8.05 (1 H, d), 3.97 (3H, s).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 106896-49-5.

Reference:
Patent; NOVARTIS AG; ASTEX THERAPEUTICS LIMITED; HOWARD, Steven; MORTENSON, Paul Neil; HISCOCK, Steven Douglas; WOOLFORD, Alison Jo-Anne; WOODHEAD, Andrew James; CHESSARI, Gianni; O’REILLY, Marc; CONGREVE, Miles Stuart; DAGOSTIN, Claudio; CHO, Young Shin; YANG, Fan; CHEN, Christine Hiu-Tung; BRAIN, Christopher Thomas; LAGU, Bharat; WANG, Yaping; KIM, Sunkyu; GRIALDES, John; LUZZIO, Michael Joseph; PEREZ, Lawrence Blas; WO2010/125402; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 17100-65-1, name is Methyl 2-bromo-4-methoxybenzoate, its 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. SDS of cas: 17100-65-1

General procedure: Argon was bubbledthrough a mixture of boronic acid 13 [27] (1.43 g, 4.65 mmol), methyl 2-bromo-4-methoxybenzoate (14, 950mg, 3.88 mmol), and Cs2CO3 (5.06 g, 15.5 mmol) in DME/H2O (5:1, 10.5 mL of DME and 2.1 mL ofH2O) for 10 min. The Pd(PPh3)4 (448 mg, 0.39 mmol) catalyst was added to the mixture while argonbubbling was maintained through the mixture, and degassing was continued for an additional 5 min.The reaction mixture was microwaved with stirring at 110 C for 45 min in a Biotage apparatus [25].Then, the mixture was cooled to room temperature and filtered through a short celite pad. Volatileswere removed under reduced pressure, and Et2O was added. The ethereal solution was washed withwater and brine, dried over MgSO4, and concentrated under reduced pressure. Purification by flashcolumn chromatography on silica gel (10-30% EtOAc/hexane) gave 15 (1.4 g, 84% yield) as a yellow oil.

The synthetic route of Methyl 2-bromo-4-methoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Yingpeng; Ho, Thanh C.; Baradwan, Mohammed; Lopez-Alberca, Maria Pascual; Iliopoulos-Tsoutsouvas, Christos; Nikas, Spyros P.; Makriyannis, Alexandros; Molecules; vol. 25; 3; (2020);,
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Related Products of 82702-31-6, The chemical industry reduces the impact on the environment during synthesis 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate, I believe this compound will play a more active role in future production and life.

b) Preparation of methyl 3-bromo-4-[4-(2-hydroxyethyl)piperazin-1-yl]benzoate Methyl 3-bromo-4-fluoro benzoate (1.39 g, 5.96 mmol) was dissolved in N,N-dimethylformamide (12 mL), added 1-piperazineethanol (3.88 g, 29.8 mmol) and potassium carbonate (2.47 g, 17.9 mmol), and the mixture was stirred under microwave irradiation at 100 C. for 0.5 hours. The reaction solution was added water at room temperature, extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/acetone). The title compound (730 mg (yield 36%)) was obtained as a yellow oil. 1H-NMR (CDCl3) delta: 2.64 (2H, t, J=5.1 Hz), 2.71-2.75 (5H, m), 3.15-3.19 (4H, m), 3.67 (2H, t, J=5.1 Hz), 3.89 (3H, s), 7.03 (1H, d, J=8.6 Hz), 7.94 (1H, dd, J=1.6, 8.6 Hz), 8.22 (1H, d, J=1.6 Hz).

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-bromo-4-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KOWA COMPANY, LTD.; US2010/280013; (2010); 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. 69038-74-0, name is tert-Butyl 3-Bromobenzoate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

Reference example 22 tert-Butyl 3-allylbenzoate To a solution of isopropylmagnesium bromide (0.76M THF solution, 26ml, 20mmol) in THF (16ml) was dropped at 0C butyllithium (1.59M hexane solution, 25ml, 40mmol), and the mixture was stirred for 15 minutes, followed by stirring for 20 minutes at -78C. Thereto was dropped a solution of tert-butyl 3-bromobenzoate (2.0g, 8.0mmol) in THF (16ml) and the solution was stirred at -78C for 30minutes. Thereto were added aryl bromide (2.8ml, 32mmol) and copper (I)cyanide (1M THF solution, 2.4ml, 2.4mmol) and the mixture was stirred for additional 1 hour. The reaction was quenched with an aqueous saturated ammonium chloride solution and extracted with hexane (30 ml*3). The organic layer was concentrated and the residue was purified by column chromatography (SiO2 60 g, elute: Hex/AcOEt=300/1) to give the titled compound as a colorless liquid (1.0g, 4.6mmol). Yield: 58% 1H NMR(CDCl3)delta 7.84-7.82(2H, m), 7.36-7.26(2H, m), 6.00-5.92(1H, m), 5.12-5.06(2H, m), 3.43(2H, d, J = 6.7 Hz), 1.60(9H, 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:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; AstraZeneca AB; EP1728792; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 40876-98-0, 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. 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, This compound has unique chemical properties. The synthetic route is as follows.

[0713] Step 2: Synthesis of ethyl 6-hydroxy-lH-pyrazolo[3,4-b]pyridine-4-carboxylate [0714] A stirred solution of lH-pyrazol-3 -amine (45 g, 542 mmol) in acetic acid (297 mL) and water (900 mL) was cooled to 0 C and diethyl oxaloacetate sodium salt (1 13.85 g:542.16 mmol) was added to it. Resulting solution was heated at 100 C for overnight. After completion of reaction, solid was filtered and dried to obtain the desired intermediate (25 g, 22%).

The chemical industry reduces the impact on the environment during synthesis Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; EPIZYME, INC.; KUNTZ, Kevin, Wayne; OLHAVA, Edward, James; CHESWORTH, Richard; DUNCAN, Kenneth, William; WO2012/118812; (2012); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 88709-17-5, name is Ethyl 2-ethoxy-4-methylbenzoate, 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 88709-17-5, HPLC of Formula: C12H16O3

To the suspension of 700 ml of cyclo hexane, 86 g (1.0 mol) of N-bromo succinimide and 3 g (0.03 mol) of AIBN was added 100 g (1.0 ml) of Ethyl-2-ethoxy-4-methyl benzoate. Heated the resulted mass to reflux and stirred for 3-5 hr. Cooled to 50-60 C. and charged 200 ml of water, then stirred for 10-15 min. Separated the aqueous phase and organic phase. The organic phase was washed with 200 ml of 5% hydrose followed by water (200 ml) at 50-60 C. Total organic phase was distilled completely under vacuum at below 60 C. Cooled to 25-35 C. and the title compound was isolated from residue with 100 ml n-Heptane at 0-5 C. The obtained compound was recrystallised from 400 ml of n-Heptane. Dried the compound under reduced pressure at 45-50 C. The yield of the recrystallised compound is 59.2 g (43%). [0038] The obtained product was characterised by analytical techniques like IR, Mass and 1H-NMR

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-ethoxy-4-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; DR. REDDY’S LABORATORIES LIMITED; DR. REDDY’S LABORATORIES, INC; US2004/249188; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, 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 3618-04-0, SDS of cas: 3618-04-0

Chloro(1 ,1-dimethylethyl)dimethylsilane (1 15 g; 0.76 mol) was added in portions over 1 hour to a solution of commercially available ethyl 4-hydroxycyclohexanecarboxylate (118 g; 0.68 mol), imidazole (103 g; 1.52 mol) and dimethylformamide (400 ml.) stirred under an atmosphere of argon. A small exotherm was observed resulting in the reaction mixture temperature increasing to -40 0C. The mixture was stirred at room temperature overnight then poured into 10% citric acid solution (2 L) and extracted with diethyl ether (2 x 800 ml_). The ether extracts were washed with water, brine and then dried (Na2SC>4) and the solvent was removed to give the title compound as an oil (198.4 g) 1H NMR delta (CDCI3, 400 MHz): 0.01 (6H, m), 0.85 (9H, s), 1.2 (3H, m), 1.3-1.5 (2H, m), 1.6 (2H, m), 1.85-2 (3H, m), 2.15-2.3 (1 H, m) 3.5 (0.4H, m) 3.86 (1 H, m) 4.1 (1 H, m).

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; GLAXO GROUP LIMITED; WO2009/37294; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics