Category: esters-buliding-blocks

Application of 49851-36-7, These common heterocyclic compound, 49851-36-7, name is Methyl 2-(2-aminophenyl)acetate hydrochloride, 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.

ln a 40 mL vial, HATU (2.263 g, 5.95 mmol) was added in one portion at room temperature to a DMF solution (10 mL) of methyl 2-(2-aminophenyl)acetate hydrochloride (CAS 49851-36-7) (1g, 4.96 mmol), 6-chloropyridine-2-carboxylic acid (CAS 4684-94-0) (0.938 g, 5.95 mmol) and DIEA (2.165 mL, 12.40 mmol). The resulting solution was allowed to stir at room temperature (2.5 hr). The reaction was diluted with ethyl acetate, washed with water (twice) and a saturated aq. NaCI solution. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified via FCC (10:1 Heptane/ethyl acetate to 1 :1 Heptane/ethyl acetate) to give the title compound. MS (ESI+) m/z 305.3 (M+H).

Statistics shows that Methyl 2-(2-aminophenyl)acetate hydrochloride is playing an increasingly important role. we look forward to future research findings about 49851-36-7.

Reference:
Patent; NOVARTIS AG; BELANGER, David B.; FLOHR, Stefanie; GELIN, Christine Fang; JENDZA, Keith; JI, Nan; LIU, Donglei; LORTHIOIS, Edwige Liliane Jeanne; KARKI, Rajeshri Ganesh; MAINOLFI, Nello; POWERS, James J.; RANDL, Stefan Andreas; ROGEL, Olivier; VULPETTI, Anna; YOON, Taeyoung; WO2015/9977; (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. 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate, A new synthetic method of this compound is introduced below., Formula: C8H6BrFO2

Cesium carbonate ((3.1 g, 9.6 mmol) was added to 2,4-difluorophenol (0.83 g, 6.4 mmol) and methyl 3-bromo-4-fluorobenzoate (1.57 g, 6.7 mmol)In a solution of dimethyl sulfoxide (10 mL). The reaction mixture was stirred at 80 C for 12 hr, then cooled to room temperature, then water (50mL), ethyl acetate (50mL*2). The organic phase was washed with brine (25 mL*4) and evaporated to dryness. The crude product was subjected to column chromatography (peel ether: ethyl acetate = 20:1) to give methyl 3-bromo-4-(2,4-difluorophenoxy)benzoate (1.58 g, 4. 72%).

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; Shanghai Hansen Bio-pharmaceutical Technology Co., Ltd.; Jiangsu Haosen Pharmaceutical Group Co., Ltd.; Sun Changan; Zhang Xiaoyu; Chen Gangsheng; Zong Shumin; (45 pag.)CN109836385; (2019); A;,
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Related Products of 3196-15-4, The chemical industry reduces the impact on the environment during synthesis 3196-15-4, name is Methyl 2-bromobutyrate, I believe this compound will play a more active role in future production and life.

5-Ethyl-2-pyrazin-2-yl-thiazol-4-ol: A solution of pyrazine-2-carbothioamide (1 g, 7.19 mmol) in ethanol (20 ml) was treated with methyl 2-bromobutyrate (1.56 g, 992 mul, 8.62 mmol) an pyridine (853 mg, 872 mul, 10.8 mmol) and heated to reflux for 2 hours. The reaction mixture was cooled and concentrated to dryness under reduced pressure, and the resulting solid was filtered and washed with diethyl ether to provide 5-ethyl-2-pyrazin-2-yl-thiazol-4-ol (0.740 g, 50%) which was used directly without further purification. MS (M+H)=208.

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 2-bromobutyrate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-La Roche Inc; Bhagirath, Niala; Brameld, Kenneth Albert; Kennedy-Smith, Joshua; US2013/90334; (2013); A1;,
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23676-08-6, name is Methyl 4-ethoxybenzoate, 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. category: esters-buliding-blocks

General procedure: To a suspension of sodium hydride (60% in mineral oil, 5 eq) in dryTHF was added solution of substituted methyl benzoate (2 eq) in dryTHF. After mixture refluxed, substituted acetophenone (1 eq) in dryTHF was added dropwise. The mixture was refluxed overnight, then quenched with 1 N HCl. The mixture was extracted with ethyl acetatetwice, and the combined organic phase was washed with brine solution,dried with anhydrous Na2SO4, filtrated, and concentrated under reduced pressure. The residue was purified on a silica gel column.

The synthetic route of 23676-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jeong, Jieun; Kim, Kun-Hee; Kim, Dong-Young; Chandrasekaran, Gopalakrishnan; Kim, Minhee; Pagire, Suvarna H.; Dighe, Mahesh; Choi, Eun Young; Bak, Su-Min; Kim, Eun-Young; Shin, Myung-Geun; Choi, Seok-Yong; Ahn, Jin Hee; Bioorganic and Medicinal Chemistry; vol. 27; 19; (2019);,
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Application of 1130165-74-0, 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 1130165-74-0 as follows.

(1) A mixture of ethyl 4-bromo-3-fluorobenzoate (500 mg), tris(dibenzylideneacetone)dipalladium (0) (94 mg), (R)-(+)-(1,1′-binaphthalene-2,2′-diyl)bis(diphenylphosphine) (189 mg), cesium carbonate (1.98 g), (R)-pyrrolidin-3-ol (353 mg), and toluene (5 mL) was stirred for 1 hour under heating and refluxing. The reaction mixture was cooled to room temperature and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent; 70%-30% n-hexane/ethyl acetate] to obtain ethyl (R)-3-fluoro-4-(3-hydroxypyrrolidin-1-yl)benzoate (390 mg) as a brown oily substance. MS (ESI nm/z): 254 (M+H) RT (min): 1.41

According to the analysis of related databases, 1130165-74-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJIFILM Corporation; Ookubo, Megumi; Sekine, Shinichiro; Mashiko, Tomoyuki; Kawai, Hyoei; Fukunaga, Hirofumi; US2020/17459; (2020); A1;,
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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. 89-91-8, name is Methyl 2,2-dimethoxyacetate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl 2,2-dimethoxyacetate

A diethyl ether solution of ethylmagnesium bromide (concentration=2 1.85 mass %, 277 g) was added to a reaction flask and was cooled to around 0 C. by stirring on an ice-cooling bath. A Grignard reaction was carried out by the dropwise addition to this solution over one hour of methyl dimethoxyacetate (25 g). This was followed by return to room temperature and reaction for 12 hours. The reaction solution was ice-cooled; 200 g of a saturated aqueous ammonium chloride solution was added dropwise; and the pH was subsequently adjusted to around neutrality by the dropwise addition of 10 mE of a 36% hydrochloric acid solution. The solution was then transferred to a separatory funnel; the organics were extracted with 50 g of hexane and separated; and drying was carried out over an appropriate amount of magnesium sulfate. This hexane suspension was filtered followed by removal of the solvent on an oil bath at around 65 C. Distillation was performed under reduced pressure on an oil bath at around 100 C. to obtain 22.4 g of a transparent and colorless 3-dimethoxym- ethyl-3-pentanol (GC purity=96.3%). 10 g of pure water and 1 g of 36% hydrochloric acid were added under ice cooling to 7 g of the 3-dimethoxymethyl-3-pentanol and stirring was carried out overnight. After this, 9.5 g of a 33% aqueous ethylamine solution was added dropwise under ice cooling and a reaction was run for 10 hours. The pH of the reaction solution at this time was 10 to 11. When stirring was stopped, separation occurred into an aqueous layer and a small amount of an organic layer, and the organic layer was determined to be alcohol compound No. 140 according to the NMR results. 2.7 g of the target was obtained for a yield of 33%.

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 89-91-8.

Reference:
Patent; ADEKA CORPORATION; SAKURAI, Atsushi; HATASE, Masako; YOSHINO, Tomoharu; ENZU, Masaki; (40 pag.)US2017/129912; (2017); 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. 4385-35-7, name is 3-Isochromanone belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H8O2

To a suspension of isochromanone (99% pure, 149.7 g, 1.00 mol) in methanol (280 mL) was added dropwise over a period of 90 min at 14-16 C. sodium methanolate (30% in methanol, 270.0 g, 1.50 mol) and the resulting mixture was stirred for 90 min at 15 C. To this mixture was added dropwise over a period of 6.5 h at 9-13 C. iso-butyl nitrite (94% pure, 137.1 g, 1.25 mol) and the mixture was stirred at 8 C. overnight. The conversion was monitored by HPLC. After completion of the reaction, 4 M hydrochloric acid was added to adjust a pH<1 before the resulting suspension was stirred for overnight at 4 C. The crude product was collected by filtration, washed with cold dist. water (2×500 mL) and dried in vacuo at max. 45 C. Isochroman-3,4-dione-4-oxime was obtained as a colorless solid (145.9 g, 90.4 HPLC-area %, 74% yield).1H-NMR (DMSO-d6): delta=13.3 (s, 1H), 8.34 (d, J=7.4 Hz, 1H), 7.54-7.41 (m, 3H), 5.46 (s, 2H) ppm; 13C-NMR (DMSO-d6): delta=162.3, 140.2, 133.2, 130.2, 129.0, 127.9, 125.4, 125.0, 68.3 ppm; mp=179-182 C. The synthetic route of 4385-35-7 has been constantly updated, and we look forward to future research findings. Reference:
Patent; BASE SE; US2011/295022; (2011); 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. 105-53-3, name is Diethyl malonate, A new synthetic method of this compound is introduced below., COA of Formula: C7H12O4

(a) Isobutyldiethyl malonate Diethyl malonate is treated with an ethanol and sodium ethoxide mixture. Then iso-butyl bromide is added to form isobutyl diethyl malonate as the product of this malonic ester synthesis.

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; E. R. Squibb & Sons, Inc.; US4382081; (1983); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 1195768-18-3 name is Methyl 3-amino-2-fluorobenzoate, 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. 1195768-18-3

A 500 mL round-bottomed flask was charged with methyl 3-amino-2- fluorobenzoate (20 g, 1 18 mmol) and pyridine (10.52 mL, 130 mmol) in dichloromethane (DCM) (100 mL) to give a yellow/clear solution at 0 C. After 5 min, 1 -propanesulfonyl chloride (13.26 mL, 1 18 mmol) was added to the reaction and warmed to room temperature. After 24 h, the reaction mixture was diluted with EtOAc (200 mL) and concentrated to a volume of 50 mL. The reaction mixture was diluted with EtOAc (200 mL) and water (200 mL) and stirred. After stirring, the EtOAc layer was separated from the water layer. The EtOAc layer was diluted with water (200 mL). After stirring, the EtOAc layer was separated from the water layer. The EtOAc layer was dried over Na2SO4, filtered, and concentrated to 50 mL. While stirring, the reaction mixture was diluted with EtOAc (50 mL) and hexanes (200 mL) and stirred. The solids were filtered and washed with hexanes. The product was put into drying oven for 1 day to obtain methyl 2-fluoro-3- [(propylsulfonyl)amino]benzoate. 28.9 g (105 mmol, 89 % yield) MS: 276 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-2-fluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE LLC; ADAMS, Jerry, Leroy; FAITG, Thomas; KASPAREC, Jiri; PENG, Xin; RALPH, Jeffrey; RHEAULT, Tara Renae; WATERSON, Alex Gregory; WO2011/59610; (2011); A1;,
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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. 25542-62-5, name is Ethyl 6-bromohexanoate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Ethyl 6-bromohexanoate

Example 9.1 (0321) (0322) Ethyl 2-methyl acetoacetate (29.2 mL, 0.203 mol. 1 eq), 21% sodium ethoride solution (64 mL, 0.816 mol, 4 eq), ethyl 6-bromohexanoate (34 mL, 0.192 mol, 1 eq) and ethanol (200 mL) are added and the mixture is subjected to reflux at 120 C. for 12 hours. Next, the solvent is neutralized with 1M hydrochloric acid and extraction is carried out by using chloroform and distilled water. The extracted solvent is dried under reduced pressure and purification is carried out by normal phase chromatography to obtain the target compound (36.8 g, 63.4%). (0323) Rf=0.34 (Silica gel, hexane/ethyl acetate=10:1 v/v)

According to the analysis of related databases, 25542-62-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BioActs Co., Ltd.; PARK, Jin Woo; JANG, Su-Jung; KIM, Kiwon; SHIN, Gyeong Rim; LEE, Bongkyu; (52 pag.)US2017/313883; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics