Month: July 2021

Electric Literature of 701-83-7, These common heterocyclic compound, 701-83-7, name is 3-Fluorophenyl acetate, 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 23 Preparation of 4′-Fluoro-2′-hydroxyacetophenone m-Fluorophenyl acetate (123 g, 0.798 mol) is cooled with an ice-bath, treated portionwise with aluminum chloride (150 g, 1.12 mol), stirred at 190 C for one hour, and cooled to obtain a solid. A mixture of ice, water and hydrochloric acid, and methylene chloride are added to the solid.

Statistics shows that 3-Fluorophenyl acetate is playing an increasingly important role. we look forward to future research findings about 701-83-7.

Reference:
Patent; American Cyanamid Company; EP908457; (1999); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

6279-86-3, name is Triethyl methanetricarboxylate, 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. Application In Synthesis of Triethyl methanetricarboxylate

To a solution of tert-butyl [2-[1-(2-iodoethyl)cyclohexyl]ethoxy]diphenylsilane (540 mg) and ethyl methane tricarboxylate (727 mg) in N, N-dimethylformamide (5 ML) was added potassium carbonate (575 mg) at room temperature.. The solution was stirred at 110 C for 6 hours, to which water and 3N hydrochloric acid were added.. The solution was extracted with ethyl acetate.. The organic layer was washed in turn with a 1N aqueous sodium hydroxide solution, water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.. The resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=85:15) to give the title compound (470 mg).1H-NMR (CDCl3) delta: 1.03 (s, 9H), 1.17-1.40 (m, 12H), 1.23 (t, 9H, J=6.8 Hz), 1.60 (t, 2H, J=8.0 Hz), 1.96-2.04 (m, 2H), 3.68 (t, 2H, J=8.0Hz), 4.18 (q, 6H, J=6. 8 Hz), 7.73-7.45 (m, 6H), 7.64-7.70 (m, 4H).

The synthetic route of 6279-86-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyorin Pharmaceutical Co., Ltd.; Nisshin Pharma Inc.; EP1443046; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 680-65-9, 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. 680-65-9, name is Diethyl difluoromalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A SOLUTION OF COMMERCIALLY AVAILABLE DIETHYL DIFLUOROMALONATE (10.1145 g, 0.0515 mol) in anhydrous methanol (110 mL) was saturated with ammonia (g) at 0 C for 45 min. The resulting mixture was stirred in an ice bath for 3h and monitored by MS (m/z M+H 139). The product was concentrated under reduced pressure to afford desired amide 13-2 as a white powder (7.1027 g, 99%): HR-MS (ES) m/z CALCD FOR C3H4N2F202 (MH+) =139. 0314. Observed: 139.0278.

The synthetic route of Diethyl difluoromalonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA CORPRATION; WO2004/60376; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 34837-84-8, 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 34837-84-8 as follows.

To a stirred solution of diisopropylamine (13.0 g) in tetrahydrofurane (160 mL)was added a solution of n-butyllithium in hexane (51 .4 mL; c= 2.5 M) at -78 °C.The solution was stirred at 0 C for 15 minutes. The solution was cooled to -78°C and a solution of methyl (4-fluorophenyl)acetate (18.0 g), dissolved intetrahydrofurane (40 mL) was added. The solution was stirred at -78 °C for 30 minutes. Methyl iodide (10.0 mL) was added at -78 C, and the solution was allowed to warm up to 0 °C within 1 h. Water was added and the reaction mixture was extracted with ethyl acetate. The organic phase was dried (sodium sulfate) and the solvent was removed in vacuum. Silicagelchromatography gave 18.9 g of the titte compound.1H-NMR (400MHz, DMSO-d6): O [ppm] = 1.34 (d, 3H), 3.55 (s, 3H), 3.79 (q, 1H),7.08 – 7.15 (m, 2H), 7.25 – 7.32 (m, 2H).

According to the analysis of related databases, 34837-84-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; SCHIROK, Hartmut; KOSEMUND, Dirk; BRIEM, Hans; BADER, Benjamin; BOeMER, Ulf; WENGNER, Antje Margret; SIEMEISTER, Gerhard; LIENAU, Philip; STOeCKIGT, Detlef; LUeCKING, Ulrich; SCHALL, Andreas; WO2014/198594; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

5941-55-9, name is Ethyl (E)-3-Ethoxyacrylate, 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: Ethyl (E)-3-Ethoxyacrylate

EXAMPLE 23 6.0 g of ethyl 2-chloro-5-ureidobenzoate and 6.4 g of ethyl 3-ethoxyacrylate are heated at reflux temperature in 100 ml of 1,2-dimethoxyethane and subsequently heated at this temperature with 12 ml of 2N hydrochloric acid for 5 minutes. The reaction mixture is evaporated to dryness under reduced pressure and the residue is purified by chromatography on 300 g of silica gel using ethyl acetate/n-hexane (1:3) as the eluent. There is obtained ethyl 2-chloro-5-{3-[2-(ethoxycarbonyl)vinyl]ureido}-benzoate, m.p. 116-117 C.

The synthetic route of 5941-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; US4746352; (1988); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 35180-01-9, 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. 35180-01-9, name is Chloromethyl isopropyl carbonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 9 Preparation of Tenofovir Disoproxil Fumarate [0092] To a clean 3-necked 1 L round bottom flask equipped with a mechanical stirrer, thermometer socket, addition funnel and dean-stark apparatus was charged cyclohexane (400 ml) and tenofovir (50 gms, obtained from example 1) and triethyl amine (34 gms) at temperature 20 C. to 35 C. Heated to 80 C. to 85 C. and stirred for 2 hours and simultaneously removed water liberated. The solvent was removed completely from the reaction mixture by distillation under vacuum at below 65 C. and to the obtained residue N-methyl pyrrolidinone (150 ml) and triethyl amine (34 gms) were charged at 25 C. to 30 C. Heated to 50 C. to 55 C. and chloromethyl isopropyl carbonate (125 gms) was added at same temperature and stirred for 4 hours. After completion of the reaction, the reaction mass was cooled to 20 C. to 25 C. and washed with cyclohexane (200 ml). Methylene chloride (500 ml) was charged into the organic layer and stirred for 1 hour at 10 C. to 15 C. Filtered the salts formed and washed the filtrate with water (500 ml), separated the layers and charged water (500 ml) to the organic layer. Adjusted pH to 6.5 to 7.5 with 10% ammonia solution and separated the organic layer from the aqueous layer. The solvent was removed from the organic layer under vacuum at below 35 C. to obtain oily product and then the oily product was diluted with isopropanol (150 ml). [0093] In a clean another 3-necked 1 L round bottom flask equipped with a mechanical stirrer, thermometer socket and addition funnel was charged isopropanol (350 ml) and Fumaric acid (19 gms). Heated to 50 C. to 55 C. and stirred for 20 minutes and above obtained oily product solution was added at 50 C. to 55 C. Stirred for 30 minutes at this temperature and cooled to 0 C. to 5 C. Filtered the product and washed with chilled isopropanol (75 ml). The wet product was dried at 35 C. to 40 C. under reduced pressure to provide the title compound as crude (80 gms). [0094] In another clean 3-necked 1 L round bottom flask equipped with a mechanical stirrer, thermometer socket and addition funnel was charged ethyl acetate (450 ml) and crude product (80 gms) at temperature 10 C. to 15 C. Stirred the slurry for 1 hour and filtered the product and washed with chilled ethyl acetate (50 ml). The wet product was dried at 35 C. to 40 C. for 6 hours under reduced pressure to provide the title compound. [0095] Yield: 55 gms. [0096] HPLC purity: 98.9%

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, Chloromethyl isopropyl carbonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Laurus Labs Private Limited; Indukuri, Venkata Sunil Kumar; Joga, Sree Rambabu; Gorantla, Seeta Ramanjaneyulu; Chava, Satyanarayana; US2014/303368; (2014); 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. 34846-90-7, name is Methyl 3-methoxyacrylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C5H8O3

A 250-mL round-bottom flask was charged with (Rac)-tert-butyl 3-methy 1-4-oxopiperidine-1-carboxylate (5.00 g, 23.4 mmol) and purged with nitrogen. THF (47.0 ml) was introduced and the reaction mixture was cooled to -78 °C in a dry ice-acetone bath. A solution of potassium /er/-butoxide (1.6 M in THF, 19.0 mL, 29.9 mmol) was added to the reaction mixture via syringe over 5 min. Following addition, the reaction mixture was allowed to warm to 0 °C in an ice-water bath. After 30 min, the reaction mixture was cooled to -78 °C. Methyl 3 -methoxy aery late (5.29 ml, 49.2 mmol) was added dropwise to the reaction mixture via syringe over 5 min. Following addition, the reaction mixture was allowed to warm to ambient temperature. After 2 h, the resultant red reaction mixture was cooled was cooled to -78 °C. N-phenyl bis-trifluoromethane sulfonamide (13.2 g, 37.0 mmol) was added to the vigorously stirred, cooled reaction mixture in one portion and the reaction mixture was subsequently allowed to warm to 0 °C in an ice-water bath. After 1 h, saturated aqueous sodium bicarbonate solution (100 mL) and EtOAc (100 mL) were added to the reaction mixture, and the layers were separated. The aqueous layer was extracted with EtOAc (3 x 50 mL) and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography in two portions (100-g silica gel Biotage column, eluent: gradient, 0 to 30percent EtOAc in heptane) to afford a mixture of (Rac)-(E)-tert-buy 3-(3-methoxy-3-oxoprop-l-en-l-yl)-6-methyl-4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-l(2H)-carboxylate and (Rac)-(E)-tert-buy 3-(3-methoxy-3-oxoprop-l-en-l-yl)-2-methy 1-4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-l(2H)-carboxylate (11.75 g, 27.4 mmol, 117 percent yield) as a yellow solid.A 20-mL vial was charged with a mixture of (Rac)-(E)-tert-buty 1 3-(3-methoxy-3-oxoprop-l-en-l-yl)-6-methyl-4-(((lrifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-l(2H)-carboxylate and (Rac)-(E)-tert-buty 3-(3-methoxy-3-oxoprop-1 -en-1 -yl)-2-methyl-4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-l(2H)-carboxylate (716 mg, 1.668 mmol), 2,3′,5′-trifluoro-5-methoxy-[l,l’-bipheny 1]-4-amine (Preparation 4h, 352 mg, 1.39 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (101 mg, 0.174 mmol), cesium carbonate (1.36 g, 4.17 mmol), tris(dibenzylideneacetone)dipalladium(0) (63.9 mg, 0.07 mmol), and 1,4-dioxane (6.95 mL) then sparged with nitrogen for 10 min. The needle was then removed and the reaction was heated to 100 °C. After 3 h, the reaction mixture was allowed to cool to ambient temperature and was diluted with EtOAc (15 mL) and filtered through a Celite® pad. The pad was rinsed with EtOAc (3 x 15 mL). The filtrate was concentrated under reduced pressure and purified by flash column chromatography (50-g silica gel Biotage column, eluent: gradient, 0 to 35percent 3:1 EtOAc/EtOH in heptane with DCM as a 10percent additive) to afford a mixture of (Rac)-tert-butyl 7-methyl-2-oxo-l-(2,3′,5′-trifluoro-5-methoxy-[l,r-biphenyl]-4-yl)-l,2,7,8-tetrahydro-l,6-naphthyridine-6(5H)-carboxylate and (Rac)-tert-buy 5-methy 1-2-oxo-1-(2,3′,5′-lrifluoro-5-methoxy-[l, l’-bipheny l]-4-yl)-l,2,7,8-tetrahydro-l,6-naphthyridine-6(5H)-carboxylate (587 mg, 1.17 mmol, 84.0percent) as a brown solid,A 20-mL vial was charged with a mixture of (Rac)-tert-butyl 7-methyl-2-oxo-1-(2,3′,5′-trifluoro-5-methoxy-[l, l’-bipheny l]-4-yl)-l,2,7,8-tetrahydro-l,6-naphthyridine-6(5H)-carboxylate and (Rac)-tert-butyl 5-methy 1-2-oxo-1-(2,3′,5′-trifluoro-5-methoxy-[l,l’-bipheny l]-4-yl)-l,2,7,8-tetrahydro-l,6-naphthyridine-6(5H)-carboxy late (587 mg, 1.173 mmol) and trifluoroacetic acid (5.86 mL) at ambient temperature. After 30 min, the reaction mixture was concentrated under reduced pressure, dissolved in DCM (15 mL) and carefully poured into saturated aqueous sodium bicarbonate solution (15 mL). The layers were separated and the aqueous layer extracted with additional DCM (3 x 15 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure to afford a mixture of (Rac)-tert-butyl 7-methyl-2-oxo-l-(2,3′,5′-trifluoro-5-methoxy-[l,l’-biphenyl]-4-yl)-l,2,7,8-tetrahydro-l,6-naphthyridine-6(5H)-carboxylate and (Rac)-tert-butyl 5-methy 1-2-oxo-1-(2,3′,5′-lrifluoro-5-methoxy-[l, l’-bipheny l]-4-yl)-l,2,7,8-tetrahydro-l,6-naphthyridine-6(5H)-carboxylate (400 mg, 1.00 mmol, 85.0percent) as a tan amorphous solid, which was used without further purification.20-mL vial was charged with a mixture of (Rac)-tert-butyl 7-methyl-2-oxo-1-(2,3′,5′-trifluoro-5-methoxy-[l, l’-bipheny l]-4-yl)-l,2,7,8-tetrahydro-l,6-naphthyridine-6(5H)-carboxylate and (Rac)-tert-butyl 5-methy 1-2-oxo-1-(2,3′,5′-trifluoro-5-methoxy-[l,l’-bipheny l]-4-yl)-l,2,7,8-tetrahydro-l,6-naphthyridine-6(5H)-carboxylate (400 mg, 1.00 mmol), N-(isoxazol-3-yl)-2-oxooxazol…

The synthetic route of 34846-90-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; USA Anjin Corporation; M .weisi; B .C.miergelamu; T .dining; J .siteerwogen; A .gusiman-peileisi; A .beiqiao; I .E.makesi; (177 pag.)CN107531705; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 6279-86-3,Some common heterocyclic compound, 6279-86-3, name is Triethyl methanetricarboxylate, molecular formula is C10H16O6, 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 well-stirred solution of (1R)- l-(4-chlorophenyl)ethanol (1.00 g, 6.38 mmol) and triethylmethanetricarboxylate (2.69 mL, 12.8 mmol) in dry toluene (12.8 mL) under dry nitrogen is added a 1M solution of trimethylphosphine in THF (12.8 mL, 12.8 mmol) via syringe. The mixture is cooled at -78 C and DIAD (2.51 mL, 12.8 mmol) is added slowly over a period of 15 min. The reaction is stirred at -78 C for lh, the bath is removed and stirring is continued as the bath warmed to rt for an additional 4 h. The reaction mixture is concentrated, dissolved in diethyl ether (100 mL) and washed with IN NaOH (2 x 50 mL) and IN HC1 (1 x 50 mL). The organics are dried with anhydrous sodium sulfate, concentrated and the residue is subjected to silica gel chromatography (230-400 mesh, 150 g, elution with 5 and 10% ethyl acetate/hexane) to give 1.90 g of triethyl (25)-2-(4- chlorophenyl)propane-l ,l , l-tricarboxylate as an oil. NMR (400 MHz, CDC13) delta ppm 1.20 (9 H, t), 1.47 (3 H, d), 3.82 (1 H, q), 4.17 (6 H, m), 7.24 (2 H, d), 7.36 (2 H, d); MS (ESI+) for Ci 8H23C106 m/z 371.1 (M+H)+; HPLC retention time: 5.20 min. (Method D).

The synthetic route of 6279-86-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIORELIX, INC.; COISH, Philip, D., G.; DIXON, Brian, R.; OSTERMAN, David; ARISTOFF, Paul, Adrian; NAVIA, Manuel; SCIAVOLINO, Frank; AVOLA, Stephanie; BABOULAS, Nick; BELLIOTTI, Thomas, R.; BELLO, Angelica; BERMAN, Judd; CHRUSCIEL, Robert, A.; EVANS, Bruce, R.; KAUR, Harpreet; MOON, David; PHAM, Vinh; ROUGHTON, Andrew; WICKENS, Phil; WILSON, Jeffrey; WO2011/126567; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 99548-54-6, 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. 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of Compound II (200 mg) and anisole (6.0 mL) were added phenylboronic acid (117 mg), PdCl2(dppf) (64 mg), potassium iodide (435 mg) and potassium carbonate (362 mg). The mixture was stirred at room temperature for 2.5 hours under carbon monoxide (1 atm) atmosphere, and then stirred at 100C overnight. The reaction mixture was diluted with ethyl acetate, and filtered through Celite. The filtrate was washed with brine, and the organic layer was dried over sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 100/0 to 85/15) to give Compound III (105 mg).

The synthetic route of Methyl 3-bromo-2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; HORIUCHI, Yoshihiro; FUJIWARA, Hiroaki; SUDA, Hitoshi; SASAKI, Izumi; IWATA, Mitsutaka; SAWAMURA, Kiyoto; EP2612848; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 711-01-3, These common heterocyclic compound, 711-01-3, name is Methyl adamantane-1-carboxylate, 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.

Step 1 compound (10.7 g, 0.055 mmol, 1 equiv) was dissolved in anhydrous THF (150 mL) under argon and was treated with a solution of LiAIH4 (1 M in THF, 69 mL, 69 mmol, 1.25 equiv). After stirring at rt for 1.5 h, the reaction was cooled to 0C and quenched sequentially with H20 (5.1 mL), 15% aq NaOH (5.1 mL), and H20 (10.2 mL). After stirring at rt for 15 min, the slurry was vacuum filtered, and the solids washed with EtOAc (2X100 mL). The filtrate was concentrated by rotary evaporation and the resulting solid purified by flash column chromatography on SILICA GEL (5X15 cm) with 10% ETOAC/CH2CI2. This afforded the Step 2 product as a white solid (8.74 g, 96%).

Statistics shows that Methyl adamantane-1-carboxylate is playing an increasingly important role. we look forward to future research findings about 711-01-3.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2005/12249; (2005); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics