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. 70347-04-5, name is Methyl 4-methoxy-3-methylbenzoate, A new synthetic method of this compound is introduced below., Product Details of 70347-04-5

Reference example 57 Methyl 3-bromomethyl-4-methoxybenzoate To a solution of methyl 3-methyl-4-methoxybenzoate (3.0g, 16.5mmol) which was prepared in Reference example 56 in carbon tertachloride (100ml) were added N-bromosuccinimide (2.9g, 16.5mmol) and benzoyl peroxide (0.10g), and the mixture was refluxed for 6 hours. After being cooled to 0C, the precipitate was filtered, and to the filtrate was added a saturated aqueous sodium thiosulfate solution (1ml). The solution was stirred for 15 minutes and concentrated in vacuo. To the residue was added water and the solution was extracted with chloroform 50 ml*3). The organic layer was concentrated and the precipitated solid was filtered to give the titled compound as a white solid (3.0 g, 11.7 mmol). Yield: 70%. 1H NMR(CDCl3)delta 8.04-7.99(2H, m), 6.91(1H, d, J = 8.6 Hz), 4.55(2H, s), 3.97(3H, s), 3.89(3H, 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;,
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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. 178312-47-5, name is Ethyl 4,4-difluorocyclohexanecarboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 4,4-difluorocyclohexanecarboxylate

A solution of butyllithium (1.600 mL, 4.00 mmol) was added to cold (- 78 C) solution of diisopropylamine (0.565 mL, 4.00 mmol) in THF (5 mL) under nitrogen and the mixture was stirred at -78 C 1 h. A solution of ethyl 4,4- difluorocyclohexanecarboxylate (384 mg, 2 mmol) in THF (2 mL) was added at – 78 C and the mixture was stirred for 1 h. The mixture was gradually warmed to – 20 C over 2 h and then recooled to – 78 C and connected to a balloon of oxygen and stirred at – 78 C for 1 h. The reaction mixture was added satd. NaHSC solution (5 mL) and allowed to warm to rt and stirred at rt overnight. The reaction mixture was diluted with ether and organic layer separated, washed with water, brine, dried ( a2S04). Evaporation of the solvent afforded a light yellow oil which was purified by silica gel FCC (DCM) to afford ethyl 4,4-difluoro- 1 -hydroxy – cyclohexanecarboxylate as a colorless oil (143 mg). NMR (400MHz,CHLOROFORM-d) delta 4.28 (q, J= 7.3 Hz, 2 H), 2.23 (br. s, 1 H), 2.19 – 1.99 (m, 6 H), 1.83 – 1.73 (m, 2 H), 1.33 (t, J= 1.0 Hz, 3 H).1 N NaOH (0.382 mL, 0.382 mmol) was added to a solution of ethyl 4,4- difluoro-l -hydroxy cyclohexanecarboxylate (26.5 mg, 0.127 mmol) in THF (0.5 mL) and methanol (0.5 mL) and the mixture was stirred at rt overnight. The reaction mixture was acidified with 2 N HC1 and extracted with EtOAc, washed with brine and dried (MgS04). Evaporation of the solvent afforded Cap-9 as a white solid.XH NMR (400MHz, CHLOROFORM-d) delta 2.21 – 2.01 (m, 5 H), 1.92 – 1.87 (m, J= 6.8, 3.2, 3.2 Hz, 2 H), 1.86 – 1.79 (m, J= 6.7, 3.1 Hz, 2 H).

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; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (2015); A1;,
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Electric Literature of 27798-60-3, 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. 27798-60-3 name is Methyl 2-Methoxyphenylacetate, 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 bromo-(2-methoxyphenyl)acetate; A mixture of 14.6 g (81.2 mmol) of methyl (2-methoxyphenyl)acetate, 15.2 g (85.3 mmol) of Lambda/-bromosuccinimide and a catalytic amount of AIBN in tetrachloromethane (180 ml) was heated under reflux with stirring for 2h. The cooled reaction solution was filtered, and the solvent was removed in vacuo. Yield: 21.6 g (100%) of yellow oil 1H-NMR (CDCI3): 3.78 (s, 3H), 3.87 (s, 3H), 5.90 (s, 1 H), 6.88 (d, 8.31 Hz, 1 H), 6.99 (t, 7.5 Hz, 1 H), 7.32 (dt, 7.6 Hz, 1.5 Hz, 1 H), 7.61 (dd, 7.6 Hz, 1.5 Hz). MS (API-ES,pos) m/z = 259 [M+H]+

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

Reference:
Patent; ABBOTT GMBH & CO. KG; WO2008/25736; (2008); A1;,
Ester – Wikipedia,
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Application of 816-27-3, 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. 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 4-chloropyridine-3-sulfonamide (500 mg, 2.6 mmol), ethyl 2-ethoxy-2- iminoacetate (565 mg, 3.9 mmol) and DBU (790 mg, 5.2 mmol) in ethanol (10 mL) was heated in a sealed tube at 150 C for 0.5 h then cooled to r.t.. The mixture was diluted with water (5 mL), adjusted to pH 5 with 1 M aqueous HCI and exacted with DCM (10 mL x 3). The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by preparative TLC (MeOH/DCM = 1 :20, v/v) to give the product as a yellow solid (100 mg, 15% yield). LCMS (ES-API) Rt 0.47 min; m/z 256 [M+H]+. 1H NMR (400 MHz, d6-DMSO), 9.05 (s, 1H), 8.76 (d, J = 5.6 Hz, 1H), 7.64 (d, J = 5.6 Hz, 1H), 4.40 (q, J = 7.2 Hz, 2H), 1.37 (t, J = 7.2 Hz, 3H).

The synthetic route of Ethyl 2-ethoxy-2-iminoacetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CTXT PTY LIMITED; MORROW, Benjamin Joseph; FOITZIK, Richard Charles; CAMERINO, Michelle Ang; LAGIAKOS, Helen Rachel; WALKER, Scott Raymond; BOZIKIS, Ylva Elisabet Bergman; STEVENSON, Graeme Irvine; CUZZUPE, Anthony Nicholas; STUPPLE, Paul Anthony; (313 pag.)WO2019/43139; (2019); A1;,
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Reference of 46064-79-3, A common heterocyclic compound, 46064-79-3, name is Methyl 3-amino-4-bromobenzoate, molecular formula is C8H8BrNO2, 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.

The intermediate compound prepared in step 4 (100 mg, 0.26 mmol) to N, N-dimethylformamide (2.6 ml) was addedAnd methyl 3-amino-4-bromobenzoate (59.8 mg, 0.26 mmol)And bis (triphenylphosphine) palladium (II) dichloride (21 mg, 0.03 mmol),Copper (I) iodide (5.7 mg, 0.03 mmol),Triethylamine (0.1 ml, 0.8 mmol) was added thereto, followed by stirring at 80 C for 4 hours.The reaction mixture was diluted with ethyl acetate and washed with distilled water.Dried over magnesium sulfate, filtered, concentrated and purified by silica gel chromatography to obtain the intermediate compound methyl 3-Amino-4 – ((2-chloro-4 – ((5- cyclopropyl-3- (2,6-dichlorophenyl)Isoxazol-4-yl) methoxy)Phenyl) ethynyl) benzoate (98.9 mg, 67%).

The synthetic route of 46064-79-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ildong Pharmaceutical Co., Ltd.; Kang Jae-hun; Lee Hong-seop; Lee Yun-seok; Jeong Jin-a; Kwon Seong-uk; Kim Gyeong-seon; Song Dong-geun; Choi Ji-hye; Hwang Hye-min; (43 pag.)KR2018/115126; (2018); A;,
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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. 116419-94-4, name is Methyl 4-methyl-3-(trifluoromethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

To a solution of methyl-4-methyl-3-(trifluoromethyl) benzoate (1 equiv) in chloroform was added N-bromosuccinimide (1.1 equiv) and benzoyl peroxide (0.01 equiv). The reaction mixture was heated at reflux overnight (18h). It was then cooled to room temperature, washed with water, dried over Na2S0 and concentrated. It was purified by silica gel chromatography (eluted with 1% ethyl acetate/hexane) to provide the title compound (65% yield). ESI MS m/z -297.

According to the analysis of related databases, 116419-94-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NATCO PHARMA LIMITED; KOMPELLA, Amala; GAMPA, Venugopala Krishna; GANGANAMONI, Srinivasulu; SIRIGIREDDY, Balakrishna Reddy; ADIBHATLA, Kali Satya Bhujanga Rao; NANNAPANENI, Venkaiah Chowdary; WO2015/186137; (2015); 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. 91085-56-2, name is Ethyl 3,5-dichlorobenzoate, A new synthetic method of this compound is introduced below., name: Ethyl 3,5-dichlorobenzoate

5,6-Dihydro-cyclopenta[b]thiophen-4-one (2.1 g, 15.0 mmol) in 15 ml of THF was treated with NaH (60 percent, 1.5 g, 36 mmol). After the addition of 3,5-Dichloro-benzoic acid ethyl ester, the reaction mixture was heated at 100 C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was added with ethyl acetate (70 mL). The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(3,5-Dichloro-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (1.5 g, 4.8 mmol) as brown solid in 34% yield.

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; DEVELOPMENT CENTER FOR BIOTECHNOLOGY; LIAO, Chu-Bin; CHIANG, Chao-Cheng; YANG, Huei-Ru; LIAO, Yuan-Chun; CHEN, Paonien; US2013/274255; (2013); A1;,
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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. 2051-59-4, name is 6-Chloro-2H-chromen-2-one belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 6-Chloro-2H-chromen-2-one

General procedure: A flame-dried reaction vessel with a magnetic stirring bar was sequentially charged with coumarin or p-dimethoxybenzene or 7-(2-Chloroethyl)theophylline (0.4mmol), PC (0.004mmol), pyridine N-oxide (0.82mmol, 78mg), CH2Cl2 (0.5mL) and CH3CN (0.5mL). Trifluoroacetic anhydride (0.8mmol, 168mg) was then added to the resulting homogeneous solution. The mixture was stirred at room temperature under irradiation from a blue LED. The solvent in the reaction mixture was removed under reduced pressure. The residue was redissolved in 2mL of CH3CN, and extracted 5 times with hexane (5mL each time). The PC was extracted into the hexane layer and separated for use in the next reaction. The CH3CN layer was dried with Na2SO4 and concentrated under vacuum. After separation and evaporation, the residue was purified by column chromatography on silica gel (200-300 mesh size) using petroleum ether/EtOAc as the eluent to give the trifluoromethyl coumarin.

The synthetic route of 2051-59-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Xiaodan; Li, Yaming; Hao, Xinyu; Jin, Kun; Zhang, Rong; Duan, Chunying; Tetrahedron; vol. 74; 15; (2018); p. 1742 – 1748;,
Ester – Wikipedia,
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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. 20330-90-9, name is Dimethyl 5-chloroisophthalate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Dimethyl 5-chloroisophthalate

To a solution of 1,3-dimethyl 5-chlorobenzene-l ,3-dicarboxylate (4.00 g, 17.5 mmol) in dioxane (50 mL) and water (50 mL) was added NaOH (700 mg, 17.5 mmol). The resulting suspension was stirred vigorously at 40C for 2 hrs and then for a further 16 hrs at room temperature. The reaction mixture was evaporated to dryness, re-dissolved in water (-200 mL) and acidified to pH 3 using 1M HCl. The resulting white precipitate was sonicated for 2 mins and filtered. The white solid was washed further with water and then dried in a vacuum oven overnight. This afforded a white solid (3.6 g) which was a mixture of 3 products including 3-chloro-5-(methoxycarbonyl)benzoic acid. This solid was dissolved in DMF (150 mL) at 0C and diethylamine (2.56 g, 0.03 mol), DIPEA (6.09 ml, 0.03 mol) and HATU (6.64 g, 0.02 mol) were added. The reaction mixture was then stirred at room temperature for 6 hrs then evaporated to dryness, re- dissolved in EtOAc (200 mL) and washed with water (3 x 200 mL) and brine (2 X200 mL). The combined organics were then dried over MgSC>4 and evaporated to dryness to afford the crude product. This was purified by silica chromatography (Biotage: lOOg SNAP cartridge) eluting with 0-80% EtOAc in heptane to afford the title compound as a colourless oil (880 mg (28%); H NMR (500 MHz, CDC13) 5 1.13 (br. s, 3H), 1.26 (t, 3H), 3.24 (br.s, 2H), 3.54 (br. s, 2H), 3.93 (s, 3H),7.55 (m, 1H), 7.92 (m, 1H), 8.04 (m, 1H).

The synthetic route of 20330-90-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTIVE BIOTECH AB; FRITZSON, Ingela; LIBERG, David; EAST, Stephen; MACKINNON, Colin; PREVOST, Natacha; WO2014/184234; (2014); A1;,
Ester – Wikipedia,
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Electric Literature of 89-91-8, 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. 89-91-8, name is Methyl 2,2-dimethoxyacetate, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 55a: heptyl 2,2-bis(heptyloxy)acetate To a solution of methyl 2,2-dimethoxyacetate (5.0g, 37.3 mmol) in heptanol (26.3 ml_, 186 mmol) was added camphorsulfonic acid (0.43g, 1.86 mmol), and the reaction was heated to 100 C, overnight. The reaction was cooled to ambient temperature and concentrated under reduced pressure. The concentrate was purified on silica gel with dichloromethane / heptane as eluent to provide 4.0g of the desired compound. 1H NMR (400 MHz, CDCI3): delta = 4.86 (s, 1 H), 4.21 (t, J = 6.78 Hz, 2H), 3.52-3.69 (m, 4H), 1.55-1.77 (m, 6H), 1.20-1.45 (m, 24H), 0.82- 0.98 (m, 9H) ppm.

The chemical industry reduces the impact on the environment during synthesis Methyl 2,2-dimethoxyacetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; BRITO, Luis; CHEN, Delai; GAMBER, Gabriel Grant; GEALL, Andrew; LOVE, Kevin; ZABAWA, Thomas; ZECRI, Frederic; WO2015/95346; (2015); A1;,
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