Month: June 2021

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;,
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Synthetic Route of 454-31-9,Some common heterocyclic compound, 454-31-9, name is Ethyl 2,2-difluoroacetate, molecular formula is C4H6F2O2, 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.

109 g (0.88 mol) of ethyl alpha, alpha-difluoroacetate was added to a stainless steel pressure-proof reaction vessel,0.107 g (0.18 mmol) of a ruthenium catalyst represented by the following formula42 g of sodium methoxide 28% methanol solution (0.22 mol of sodium methoxide)Methanol 290mL,The reactor was replaced with hydrogen 5 times,The hydrogen pressure was set to 1.0 MPa,After stirring at 15 C for 8 hours,React.After 19F-NMR analysis of the reaction, the conversion of alpha, alpha-difluoroacetic acid ethyl ester was 65%, and the selection of DFAL-EtOHThe rate is 91%. 19F-NMR was quantified with the internal standard substance alpha, alpha, alpha-trifluorotoluene.To the reaction solution was added 13.2 g (0.22 mol) of acetic acid,Then adjusting the pH to 8, judging that it is substantially neutral,Abort add.The liquid was directly distilled (bottom temperature ~ 66 C,Decompression degree ~ 2.1 kPa) to obtain a methanol solution containing DFAL-EtOH.The solution was distilled (theoretical plates 35 plates,Distillation temperature 92 ,Decompression degree ~ 35kPa) Most of the methanol separation.To a still pot (bottom) were added 96 g (2.08 mol) of ethanol,Continue distillation,45.9 g of DFAL-EtOH was obtained as a fraction.

The synthetic route of 454-31-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Center Xiaozi Co., Ltd.; Mu Cunzhenren; Qiu Yejinye; Wu Tianjiangzhang; Tian Zhongyishu; Teng Benyalong; (13 pag.)CN107438592; (2017); A;,
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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. 1186-73-8, name is Trimethyl methanetricarboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 1186-73-8

Step 1: Methyl l-(2,4-dimethoxybenzyl)-4-hydroxy-2-oxo-9-tosyl-2,5,6,9-tetrahydro- 1H-pyrido[2′,3′:4,5]thiepino[3,2-f]indole-3-carboxylate o a stirring solution of Intermediate 9 (1.02 g, 2.75 mmol), (2,4-dimethoxyphenyl)methanamine (0.51 g, 0.45 mL, 3.03 mmol), triethylamine (0.83 g, 1.14 mL, 8.25 mmol) in CH2C12(6.0 mL) at 0 C was added a solution of TiCl4(1M in CH2C12,1.4 mL, 1.4 mmol) dropwise. After the addition, the mixture was brought to roomtemperature and stirred overnight. The reaction was quenched with satd. NaHC03solution (3 mL) and the mixture was diluted with CH2C12(12 mL). The CH2C12layer was separated and the aqueous layer was extracted with CH2C12(2 x 3 mL). The combined organics were evaporated to dryness followed by the addition of trimethyl methanetricarboxylate (1.05 g,5.5 mmol) and diphenyl ether (5.0 mL). The mixture was stirred at 230 C for 10 min, then cooled to room temperature and loaded directly onto a silica gel column. The product was chromato graphed (ethyl acetate in CH2C120-50 %) to furnish the title compound as a light brown solid (1.10 g, 62%). LC-MS: 647.2 [M+H]+, RT 1.57 min.

The synthetic route of 1186-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; GERASYUTO, Aleksey, Igorevich; ARNOLD, Michael, A.; CHEN, Guangming; KARP, Gary, Mitchell; QI, Hongyan; TURPOFF, Anthony, A.; WANG, Jiashi; WOLL, Matthew, G.; ZHANG, Nanjing; ZHANG, Xiaoyan; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Marla, L.; (229 pag.)WO2016/25932; (2016); A1;,
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Synthetic Route of 87-13-8, 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. 87-13-8, name is Diethyl 2-(ethoxymethylene)malonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of aniline (25.6 g, 0.275 mol) and diethyl 2- (ethoxymethylene)malonate (62.4 g, 0.288 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. XH NMR (DMSO-ifc) delta 11.00 (d, 1H), 8.54 (d, = 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).

The synthetic route of Diethyl 2-(ethoxymethylene)malonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; HASELTINE, Eric L.; MOSKOWITZ, Samuel; ROBERTSON, Sarah; WALTZ, David; (169 pag.)WO2019/18395; (2019); A1;,
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Related Products of 99548-54-6, These common heterocyclic compound, 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate, 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.

General procedure: Aryl halide (1.0 mmol), arylboronic acid (1.2 mmol), K2CO3 (2.0 mmol), Pd(at)Al2O3-agarose (100 mg) and EtOH (5 mL) were added to a Schlenk flask. The mixture was stirred at room temperature under air. Upon complete consumption of starting materials as determined by TLC analysis, the solid was filtered and washed with acetone (3 × 5 mL). The combined organic solvents were concentrated in vacuum to afford product which was purified by silica gel column chromatography (petroleum ether/EtOAc = 10:1).

Statistics shows that Methyl 3-bromo-2-methylbenzoate is playing an increasingly important role. we look forward to future research findings about 99548-54-6.

Reference:
Article; Wang, Peng; Cai, Jin; Chen, Junqing; Ji, Min; Journal of the Brazilian Chemical Society; vol. 26; 4; (2015); p. 748 – 754;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 56441-97-5, name is Methyl 4-(benzyloxy)-3-methoxybenzoate, 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 56441-97-5, Quality Control of Methyl 4-(benzyloxy)-3-methoxybenzoate

A 250 mL, round-bottomed flask with a stirring bar, a solution of 4-hydroxy-3-methoxybenzoic acid (20 g, 118.94 mmol) was added slowly to a solution of methanol (100 mL) and concentrated sulfuric acid (10 mL). After being stirred for 12 h at reflux, saturated solution of sodium bicarbonate was added to adjust the pH to 7. Dichloromethane was added and the mixture was then filtered and the organic phase evaporated on a rotary evaporator and to obtain the compound 2 (20.37 g, 94 %). Compound 2 (20.4 g, 111.98 mmol) was added into a 500 mL, round-bottomed flask with a stirring bar, then benzyl bromide (18 mL), potassium carbonate (22 g, 156.8 mmol), DMF (200 mL) were added. It was stirred for 6 h at 80 C. Then the reaction system was poured into right amount of water, white solid (3) was obtained by filtration (28.97 g, 95 %). Compound 3 (16.54 g, 60.74 mmol) was dissolved in CH3COOH (50 mL) and then added into a 250 mL, round bottomed flask with a stirring bar. Then HNO3 (25 mL) was added into the system slowly to keep the temperature of the reaction above 5 C. The reaction temperature was raised to 50 C and kept for another 2 h. After that the system was poured into water and pale yellow solid (I) was obtained6-8 (18.3 g, 95%, m.p.: 134-135 C).

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:
Article; Wang, Kai; Zhang, Xiu-Qin; Zhu, Jian; Chen, Qiang; Zhang, Zhong-Qiang; Fan, Li; Asian Journal of Chemistry; vol. 27; 7; (2015); p. 2647 – 2650;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 75567-84-9, name is Methyl 3-(4-bromophenyl)propanoate, 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. Safety of Methyl 3-(4-bromophenyl)propanoate

To a 100 mL two-neck flask were added (R) -tert-butyl 3-oxohexahydroimidazo [1, 5-a] pyrazine-7 (1H) -carboxylate (228 mg, 0.95 mmol) , methyl 3- (4-bromophenyl) propionate (230 mg, 0.95 mmol) , tris (dibenzylideneacetone) dipalladium (87 mg, 0.095 mmol) , 2-di-tert-butylphosphino-2′, 4′, 6′-triisopropylbiphenyl (80 mg, 0.19 mmol) , cesium carbonate (0.62 g, 1.89 mmol) and 1, 4-dioxane (10 mL) . The mixture was stirred at 90 for 2 hours, and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 1/1) to give the title compound as a white solid (171 mg, 45%) . MS (ESI, pos. ion) m/z: 426.1 [M+Na] +.

The synthetic route of Methyl 3-(4-bromophenyl)propanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Xinchang; REN, Qingyun; YAN, Guanghua; GOLDMANN, Siegfried; ZHANG, Yingjun; (253 pag.)WO2019/76310; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 816-27-3,Some common heterocyclic compound, 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, molecular formula is C6H11NO3, 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.

A mixture of (3-chloro-quinolin-6-yl)-acetic acid hydrazide (4.0 g, 16.97 mmol, 1.0 eq) and ethoxy-imino-acetic acid ethyl ester (4.9 g, 33.95 mmol, 2.0 eq) in EtOH (200 mL) and AcOH (10 mL) was stirred at rt for 30 min, and then concentrated. The resulting residue was dried in vacuo to afford amino-{[2-(3-chloro-quinolin-6-yl)-acetyl]-hydrazono}-acetic acid ethyl ester (5.0 g, 89%) as a white solid.

The synthetic route of 816-27-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (183 pag.)WO2019/142053; (2019); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 756525-95-8, These common heterocyclic compound, 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, 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.

To a dried scintillation vial containing a magnetic stir bar was added tert-butyl 4-oxopiperidine-1-carboxylate (399 mg, 2 mmol), H2N-PEG2-COOt-Bu (550 mg, 2.4 mmol), 4 A molecular sieves (activated powder, 200 mg), and 1,2-dichloroethane (5 mL). The mixture was stirred for 1 h at room temperature. To the reaction mixture was added sodium triacetoxyborohydride (845 mg, 4 mmol). The mixture was stirred for 3 days at room temperature. The resulting mixture was partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 850 mg of compound 211 as a viscous oil. MS (ESI) mlz: [M+HjCalcd for C21H41N206 417.3; Found 417.2.

The synthetic route of 756525-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; R.P. SCHERER TECHNOLOGIES, LLC; RABUKA, David; MCFARLAND, Jesse M.; DRAKE, Penelope M.; BARFIELD, Robyn M.; (195 pag.)WO2017/83306; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

2065-23-8, name is Methyl 2-phenoxyacetate, 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: Methyl 2-phenoxyacetate

To a solution of 55 mg (1.00 mmol) of propargyl amine (2), in dry MTBE (2 mL) in a screwcapSchlenk vessel, were added 1.5 mmol of the methyl ester 1 (for experimental details seeTable 1) and Novozyme 435 (50 % w/w of corresponding ester substrate used) and thereaction was shaken in an incubating shaker at 45 C for 4 or 24 h (depending upon the natureof ester used). After the reaction time, the enzyme beads were filtered off and the filtrate wassubjected to column chromatography on silica gel (n-hexane/ethylacetate 1:1 or 2:1) to obtainthe pure product 3.

The synthetic route of 2065-23-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hassan, Sidra; Tschersich, Roxanne; Mueller, Thomas J.J.; Tetrahedron Letters; vol. 54; 35; (2013); p. 4641 – 4644;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics