Tag: M.W=100-200

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;,
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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;,
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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;,
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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;,
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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;,
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Related Products of 94994-25-9, A common heterocyclic compound, 94994-25-9, name is Methyl 4-formylbicyclo[2.2.2]octane-1-carboxylate, molecular formula is C11H16O3, 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.

Intermediate A51M: Methyl 4-(difluoromethyl)bicyclo[2.2.2]octane-1-carboxylate To a solution of Intermediate A51L (400 mg, 2.038 mmol) at 0 C. in CH2Cl2 (8 mL) was added DAST (0.673 mL, 5.10 mmol). The reaction mixture was stirred at RT overnight. The reaction mixture was cooled to 0 C. and carefully quenched with a solution of NaHCO3. The layers were separated. The aqueous layer was extracted with CH2Cl2. The combined organic layer was washed with brine, dried over Na2SO4, and filtered. The filtrate was concentrated. The residue was purified by silica gel chromatography (40 g REDISEP column, eluting with 0-20% EtOAc in hexane). Fractions containing the product were combined and evaporated to afford Intermediate A51M (280 mg, 62.9%). MS(ES): m/z=199 [M+H]+; 1H NMR (400 MHz, chloroform-d) delta ppm 5.54-5.26 (m, 1H), 3.68 (s, 3H), 1.89-1.76 (m, 6H), 1.65-1.50 (m, 6H).

The synthetic route of 94994-25-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; Velaparthi, Upender; Darne, Chetan Padmakar; Liu, Peiying; Wittman, Mark D.; Pearce, Bradley C.; Araujo, Erika M. V.; Dasgupta, Bireshwar; Nair, Jalathi Surendran; Janakiraman, Sakthi Kumaran; Rachamreddy, Chandrasekhar Reddy; Rao, Mettu Mallikarjuna; Karuppiah, Arul Mozhi Selvan Subbiah; Reddy, Bandreddy Subba; Nagalakshmi, Pulicharla; Bora, Rajesh Onkardas; Maheshwarappa, Shilpa Holehatti; Kumaravel, Selvakumar; Mullick, Dibakar; Sistla, Ramesh; (353 pag.)US9273058; (2016); B2;,
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Reference of 4630-80-2,Some common heterocyclic compound, 4630-80-2, name is Methyl cyclopentanecarboxylate, molecular formula is C7H12O2, 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 168 Preparation of 1-(4-Bromobutyl)cyclopentane Carboxylic Acid Methyl Ester To a solution of diisopropylamine (150 mmol, 21 mL) in THF (100 mL) was added dropwise a solution of n-butyl lithium (145 mmol, 58 mL, 2.5M) in hexanes at -10 C. while maintaining the temperature below 0 C. After addition, the solution was stirred for 30 min at 0 C. To this a solution of methyl cyclopentane carboxylate (100 mmol, 13.1 g) in THF (20 mL) was added dropwise at -70 C. maintaining the internal temperature between -60 to -70 C. After addition, the reaction mixture was stirred for 1 h at -50 to -60 C. Then, a solution of 1,4-dibromobutane (100 mmol, 21.59 g) in THF (20 mL) was added dropwise and the light brown suspension was stirred for 1 h at -60 to -70 C. Then, it was allowed to warm to room temperature and stirred overnight. The reaction mixture was poured into a saturated solution of ammonium chloride (200 mL) and the organic compound was extracted into ether (2*100 mL). The combined extracts were washed with a saturated brine solution (150 mL) and dried over anhydrous magnesium sulfate. After filtration of the drying agent, the solution was concentrated under vacuum and the resulting residue was distilled at 120-133 C./2.5 mm Hg to obtain 1-(4-bromobutyl)cyclopentane carboxylic acid methyl ester as a colorless oil (12.8 g, 48%). HR MS (C11H19BrO2): Obs mass, a 262.0565. Calcd mass, 262.0568 (M+).

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

Reference:
Patent; Hoffmann-La Roche Inc.; US6455550; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 5445-17-0, name is Methyl 2-bromopropanoate, 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 5445-17-0, Recommanded Product: Methyl 2-bromopropanoate

A solution of 1-(5-trifluoromethyl-pyridin-2-yl)-piperazine (0.9 g, 3.9 mmoles) in MeOH (13 mL) and DIPEA (1.5 mL) was treated with 2-bromo-propionic acid methyl ester (0.48 mL, 4.3 mmoles) and stirred overnight at 70 C. MeOH was removed under reduced pressure and the residue was purified (silica gel, 10-40% acetone in hexane) to provide the title compound as a yellowish solid (1.23 g, 99%).

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

Reference:
Patent; Hoff, Ethan D.; Link, James T.; Pliushchev, Marina A.; Rohde, Jeffrey J.; Winn, Martin; US2005/245532; (2005); A1;,
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Electric Literature of 83881-47-4,Some common heterocyclic compound, 83881-47-4, name is Methyl 2-(2-chloroethoxy)acetate, molecular formula is C5H9ClO3, 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.

11. Levorotatory dimaleate of methyl 2-[2-[4-[(4-chlorophenyl)phenylmethyl ]-1-piperazinyl]ethoxy]acetate. 46 g (0.16 mole) of levorotatory (-)-1-[(4-chlorophenyl)phenylmethyl]piperazine (prepared in Example 4.1), 36.6 g (0.24 mole) of methyl (2-chloroethoxy)acetate, 37.3 g (0.35 mole) of anhydrous sodium carbonate and 1.05 g(0.0064 mole) of potassium iodide are suspended in 46 ml of toluene. The suspension is heated with stirring for 18 hours at reflux temperature, then cooled to ambient temperature and filtered. The solids are washed with 100 ml of toluene and the filtrate and the washing solvent are combined. The toluene is evaporated at 50 C. under reduced pressure in a rotating evaporator. 76 g of a brown oil are obtained and are taken up in 80 ml of dichloromethane. The solution is purified by chromatography (silica column (15 to 40 mum) 1 kg; eluent: pure dichloromethane gradually diluted with methanol up to a maximum of 2% of methanol (v/v)). 43.5 g of methyl 2-[2-[ 4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetate in the form of an oil are thus obtained. Yield: 67.5%.

The synthetic route of 83881-47-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; U C B, S.A.; US5478941; (1995); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 924-99-2, A common heterocyclic compound, 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, molecular formula is C7H13NO2, 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: Ethyl 4-(4-chlorophenyl)-2-thioxo-1,2,3,4-tertahydropyrimidine-5-carboxylate 6a (Table 2, entry 1). To a mixture of thiourea 12a (23.0 mg, 0.302 mmol), 4-chlorobenzaldehyde 13a (63.0 mg, 0.448 mmol), and ethyl 3-dimethylaminoacrylate 9 (64.0 mg, 0.447 mmol) in anhydrous DMF (0.3 mL) was added anhydrous aluminum chloride (8.0 mg, 0.0600 mmol) at room temperature, and the reaction mixture was stirred at 110 C for 3 h. To the mixture was added EtOAc (10 mL) and 1 M HCl aqueous solution (5 mL), and the organic layer was separated. The aqueous layer was extracted with EtOAc (10 mL), and the combined organic layers were washed with water (5 mL) and brine (5 mL), dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography [n-hexane-EtOAc (4:1 to 2:1)] to give 6a (78.9 mg, 0.266 mmol, 88%) as pale yellow crystals.

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:
Article; Arai, Rie; Cho, Hidetsura; Gokurakuji, Yuki; Kikuchi, Hidetomo; Kubo, Takanori; Nakamura, Yuri; Nishimura, Yoshio; Sunaga, Katsuyoshi; Yuan, Bo; Tetrahedron Letters; (2020);,
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