Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 1186-73-8, name is Trimethyl methanetricarboxylate, 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 1186-73-8, Recommanded Product: Trimethyl methanetricarboxylate

Step 9: Methyl 10-chloro-l-(2,4-dimethoxybenzyl)-4-hydroxy-2-oxo-2,5,6,8-tetrahydro- lH-benzo[6,7]oxocino[5,4-b]pyridine-3-carboxylate 9-Chloro-N-(2,4-dimethoxybenzyl)-4,5-dihydro-lH-benzo[c]oxocin-6(3H)-imine (ca. 0.3 g, 0.8 mmol) and trimethyl methanetricarboxylate (0.35 g, 1.8 mmol) were mixed in Ph20 (5 mL). The stirred mixture was placed onto a pre-heated heat block at 230 C and heated for 10 min after initial bubbling of MeOH was observed (occurs at approx. 160 C internal reaction temperature). The reaction mixture was cooled to room temperature, loaded directly on a silica column, eluted first with hexanes to separate Ph20 and then EtOAc/hexanes gradient (0-50%) to yield the title compound (41 mg, 11% over 2 steps) as a yellow foam. LC-MS: 484.1 [M-H]+, RT 1.45 min.

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

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 3196-15-4,Some common heterocyclic compound, 3196-15-4, name is Methyl 2-bromobutyrate, molecular formula is C5H9BrO2, 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.

Compound I-CC (3.1 g, 17.1 mmol) and aniline (1.59 g, 17.1 mmol) were dissolved in 30 mL of acetonitrile in a glass pressure tube. After the addition of potassium carbonate (4.71 g, 34.2 mmol) and potassium iodide (0.283 g, 1.71 mmol), the tube was sealed and mixture was stirred for 18 hr at 100 C. The reaction mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution. The organic phase was dried over a2S04, filtered, evaporated down and purified by silica column (hexane:EtOAc) to give Compound II-CC (1.97 g, 59%); LCMS:194.12 m/z (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-bromobutyrate, its application will become more common.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; GALEMMO, Robert, A., Jr.; ARTIS, Dean, Richard; YE, Xiaocong, Michael; AUBELE, Danielle, L.; TRUONG, Anh, P.; BOWERS, Simeon; HOM, Roy, K.; ZHU, Yong-Liang; NEITZ, R., Jeffrey; SEALY, Jennifer; ADLER, Marc; BEROZA, Paul; ANDERSON, John, P.; WO2011/79114; (2011); A1;,
Ester – Wikipedia,
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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. 1236357-65-5, name is Methyl 1-(4-bromophenyl)cyclobutanecarboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 1-(4-bromophenyl)cyclobutanecarboxylate

Methyl 1-(4-bromophenyl)cyclobutanecarboxylate under nitrogen atmosphere(1.3 g, 4.8 mmol), (R)-3-oxo hexahydroimidazo[1,5-a]pyrazine-7(1H)-carboxylic acid tert-butyl ester (1.2 g, 4.8 mmol),Tris(dibenzylideneacetone)dipalladium(440mg, 0.48mmol),2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (410 mg, 0.97 mmol) and cesium carbonate (3.1 g, 9.5 mmol) were dissolved.In 1,4-dioxane (30 mL). The reaction was carried out at 90 C for 12 h.The heating was stopped, the solid was filtered off, and the filtrate was concentrated under reduced pressure.The residue obtained was subjected to silica gel column chromatography(PE/EA(V/V)=4/1)Purified to give the title compound as a white solid(770 mg, 37%).

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Liu Xinchang; Huang Jianzhou; Zhang Yingjun; S ·geerdeman; (267 pag.)CN109111451; (2019); A;,
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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 383-62-0 as follows. Quality Control of Ethyl 2-chloro-2,2-difluoroacetate

[0068] Synthesis of Compound B: A mixture of Compound A (3g, 1 eq), K2CO3 (3.06g, 2 eq), ethyl chlorodifluoroacetate(2.2g, 1.3 eq) in DMF (20 ml), was heated at 75C overnight. The reaction was monitored by TLC. After completion, themixture was poured into cold water (50 ml) and extracted with ethyl acetate (3350 ml). The combined organic layer waswashed with water (2330 ml), saline solution (20 ml) and dried over anhydrous sodium sulfate. Purification of the crudeproduct by column chromatography (10% ethyl acetate in hexane) yielded 1 g of the desired product. 1H NMR (DMSOd6)Theoretical MS for C17H11F3NO3: 320.26; M++ 1 found, 321.1

According to the analysis of related databases, 383-62-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Artax Biopharma Inc.; GAGETE MATEOS, Andres; CASTRO PALOMINO, Julio; MARTI CLAUZEL, Luc; TORMO CARULLA, Damia; (23 pag.)EP3059232; (2016); A1;,
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Reference of 110104-60-4, These common heterocyclic compound, 110104-60-4, name is (E)-Methyl 4-chloro-3-methoxybut-2-enoate, 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.

EXAMPLE 2 Production of 4-methoxy-2(5H) thiophenone from 4-chloro-3-methoxy-2E-butenoic acid methyl ester and sodium hydrogen sulfide 11.6 g (0.14 mol) of 90 percent sodium hydrogen sulfide monohydrate is dissolved in 90 ml of methanol. A solution of 17.0 g (0.1 mol) of 96.7 percent 4-chloro-3-methoxy-2E-butenoic acid methyl ester in 10 ml of methanol is instilled into this solution at 50 C. in 4 hours. It is stirred for another 2 hours and the methanol is then distilled off under vacuum on the rotary evaporator. The residue is mixed with 100 ml of water and extracted twice with 80 ml each of methylene chloride. The organic phase is dried over sodium sulfate and concentrated by evaporation. The residue is recrystallized hot from 15 ml of ethanol. 5.12 g of yellow-colored product with a melting point of 90 C. is obtained. Further data concerning the compound is: content (GC): 96 percent; yield: 37.8 percent.

Statistics shows that (E)-Methyl 4-chloro-3-methoxybut-2-enoate is playing an increasingly important role. we look forward to future research findings about 110104-60-4.

Reference:
Patent; Lonza Ltd.; US4906759; (1990); 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. 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: 35450-36-3

Example 1; Part A: Compound 1 (20.0 g, 81.61 mmol), trimethylboroxine (13.36 ml_, 97.93 mmol),Pd(dppf)CI2 (1.0 g, 1.36 mmol), dioxane (350 ml_), water (50 ml_), and cesium carbonate (22.5 g, 163 mmol) were stirred at 110 0C (oil bath) under nitrogen for 16 hours. After cooling, the solid was removed by filtration. The solution was concentrated and purified by sgc (10:1 EtOAc/hexanes) to give 2 (12.1 g,80%).

The synthetic route of 35450-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; KOZLOWSKI, Joseph, A.; YU, Wensheng; WONG, Michael, K.C.; KIM, Seong-Heon; TONG, Ling; LAVEY, Brian, J.; SHANKAR, Bandarpalle, B.; YANG, De-Yi; FELTZ, Robert; KOSINSKI, Aneta, Maria; ZHOU, Guowei; RIZVI, Razia, K.; DAI, Chaoyang; FIRE, Luke; GIRIJAVALLABHAN, Vinay, M.; LI, Dansu; POPOVICI-MULLER, Janeta; RICHARD, Judson, E.; ROSNER, Kristin, E.; SIDDIQUI, M., Arshad; YANG, Liping; WO2010/54279; (2010); A1;,
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Synthetic Route of 55666-43-8, 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. 55666-43-8, name is tert-Butyl 3-bromopropanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To 350mg (1. 44mmol) of 2- (2, 4-dichlorophenoxy) ethanamine and 0. 2ml (1. 44mmol) of triethylamine in 30ml of [DICHLOROMETHANE] stirring at room temperature under a nitrogen atmosphere was added 0. 21 ml (1. 44mmol) aliquots, every 30 minutes, of tert-butyl bromoacetate until the starting material was completely consumed. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with [DICHLOROMETHANE] : methanol : ammonia (95: 5: 0.5) to give the title compound (300mg, 65%) as a colourless oil. ‘H-NMR [(400MHZ,] [CDC13)] [A] = 1.42-1. 45 (s, 9H), 3.03-3. 07 (t, 2H), 3.59 (s, 2H), 4.08- 4.12 (t, [2H),] 6.83-6. 88 (d, [1H),] 7.14-7. 18 (m, [1H),] 7.34-7. 37 (m, [1H).]

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

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/16583; (2004); 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. 33842-16-9, name is Methyl benzo[d][1,3]dioxole-4-carboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl benzo[d][1,3]dioxole-4-carboxylate

A mixture of the material so obtained, a 2N aqueous potassium hydroxide solution (15.5 ml) and methanol (40 ml) was stirred at ambient temperature for 2 hours. The solution was concentrated to about one quarter of the original volume and cooled in an ice bath. The mixture was acidified to pH 3.5 by the addition of a 2N aqueous hydrochloric acid solution. The resultant precipitate was collected by filtration and washed in turn with water and diethyl ether. There was thus obtained 2,3-methylenedioxybenzoic acid (1.87 g); NMR Spectrum: (DMSOd6) 6.1 (s, 1H), 6.9 (t, 1H), 7.15 (d, 1H), 7.3 (d, 1H), 13.0 (br s, 1H).

The synthetic route of 33842-16-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/4732; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 4341-76-8, name is Ethyl 2-butynoate, molecular formula is C6H8O2, 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. HPLC of Formula: C6H8O2

00727] (i) Production of ethyl 2-methylpyrazolo[l,5-a]pyridine-3-carboxylate [00728] To a suspension of 1-aminopyridinium iodide (125 g, 0.56 mmol) in N,N-dimethylformamide (1.2 L) were added ethyl 2-butynoate (54.0 g, 0.48 mmol) and potassium carbonate (79 g, 0.56 mmol) and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with water (500 mL), ethyl acetate (500 mL) and hexane (500 mL), and the precipitated solid was collected by filtration, and washed with water (500 mL). The filtrate was extracted with a mixed solvent (1.5 L x 2) of ethyl acetate/hexane (1: 1) and dried over anhydrous magnesium sulfate, and the insoluble material was filtered off. The residue obtained by concentration of the filtrate and the solid collected by filtration in the above were combined, washed with diethyl ether (25 mL) and hexane (25 mL) and dried to give the title compound (36.0 g, 37%) as a white solid. The washing solution was concentrated, and the obtained residue was washed with diethyl ether (10 mL) and hexane (10 mL) and dried to give a second crop (11.0 g, 11%) of the title compound as a white solid. The washing solution of the second crop was concentrated, and the obtained residue was purified using a pad (elution solvent: ethyl acetate/hexane=l/l) with silica gel and activated carbon in 2 layers, washed with diethyl ether (5.0 mL) and hexane (5.0 mL) and dried to give a third crop (6.5 g, 7%) of the title compound as a white solid (total yield 55%).[00729] 1H-NMR (DMSOd6, 300 MHz) delta 1.35 (3H, t, J = 7.2 Hz), 2.57 (3H, s), 4.30 (2H, q, J = 7.2 Hz), 7.09 (IH, dt, J = 1.5, 6.9 Hz), 7.49 – 7.61 (IH, m), 8.00 (IH, td, J = 1.3 Hz), 8.75 (IH, td, J = 1.0, 6.9 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4341-76-8, its application will become more common.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BANNO, Hiroshi; HIROSE, Masaaki; KURASAWA, Osamu; LANGSTON, Steven, P.; MIZUTANI, Hirotake; SHI, Zhan; VISIERS, Irache; VOS, Tricia, J.; VYSKOCIL, Stepan; WO2010/90716; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 3196-15-4,Some common heterocyclic compound, 3196-15-4, name is Methyl 2-bromobutyrate, molecular formula is C5H9BrO2, 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.

[286] Step 3: methyl 2-[5-bromo-2-(4-methylbenzoylimino)benzo[d]thiazol-3(2H)-yl]butanoate[287] To a stirred solution of N-(5-bromobenzo[d]thiazol-2-yl)-4-methylbenzamide (90 mg, 0.258 mmol) prepared in Step 2 in N,N-dimethylformamide (3.0 mL) were added methyl 2-bromobutyrate (93.9 mg, 0.519 mmol) and potassium carbonate (107 mg, 0.768 mmol). The reaction mixture was stirred at 80 ? for 3 hours. The reaction mixture was quenched with water and then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and then evaporated. The residue was purified with silica gel column chromatography (n-hexane/ethyl acetate = 10/1) to give 109.5 mg of the titled compound as a white solid (Yield: 94%)[288] 1H NMR (CDCl3, 400 MHz) delta 8.18(d, 2H), 7.56(d, 1H), 7.42(s, 2H), 7.28(d, 2H), 5.46(brs, 1H), 3.67(s, 3H), 2.47-2.54(m, 2H), 2.42(s, 3H), 0.92(t, 3H)

The synthetic route of 3196-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YUHAN CORPORATION; HUR, Youn; KIM, Dong-Hyun; KIM, Eun-Kyung; PARK, Jin-Hwi; JOO, Jae-Eun; KANG, Ho-Woong; OH, Se-Woong; KIM, Dong-Kyun; AHN, Kyoung-Kyu; WO2013/43001; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics