Month: August 2021

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. 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H7ClO4S

[1406] tert-butyl 4-((4-(methoxycarbonyl)phenyl)sulfonamido)piperidine-1-carboxylate : To a stirred solution of methyl 4-(chlorosulfonyl)benzoate (2.0 g, 8.547 mmol, 1 eq) and triethylamine (3.5 mL, 25.64 mmol, 3.0 eq.) in tetrahydrofuron was added tert-butyl 4-aminopiperidine-1-carboxylate (2.0 g, 10.25 mmol, 1.2 eq) at 0C. The mixture was allowed to warm to room temperature and stirred 18 h. The progress of the reaction was monitored by TLC (50% ethyl acetate in hexane). After completion of reaction, the reaction was diluted with ethyl acetate (200 mL), washed with water (250 mL), brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain crude. The crude was purified by flash chromatography using 30% ethyl acetate in hexane as an eluent to obtain tert-butyl 4-((4-(methoxycarbonyl)phenyl)sulfonamido)piperidine-1-carboxylate. LC-MS (m/z)=299.2 ([M+H]+- Boc group).

The synthetic route of 69812-51-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ferro Therapeutics, Inc.; Jiang, Chun; Chen, Ruihong; Pandey, Anjali; Kalita, Biswajit; Duraiswamy, Athisayamani Jeyaraj; (293 pag.)US2019/263802; (2019); A1;,
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Reference of 61644-18-6, 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 61644-18-6 as follows.

General procedure: Carboxylic acid (±)-9 (5.18 mmol) was dissolved in N,N-dimethylformamide (15.5 mL). Cesium carbonate (4.14 mmol) was added to the solution and the suspension was stirred during 2-3 min after which chloromethyl 2-methylpropanoate (6.73 mmol) was added. After stirring at room temperature during 18-24 h, dichloromethane (30 mL) was added to the mixture and the resulting organic phase was successively washed with water (3×20 mL) and brine (3×20 mL). Organic solvent was eliminated and the residue was submitted to flash chromatography (hexane/ethyl acetate mixtures) to yield the corresponding diester (±)-5.

According to the analysis of related databases, 61644-18-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Torres, Susana Y.; Ochoa, Estael; Verdecia, Yamila; Rebolledo, Francisca; Tetrahedron; vol. 70; 31; (2014); p. 4675 – 4684;,
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394-35-4, name is Methyl 2-fluorobenzoate, 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. Safety of Methyl 2-fluorobenzoate

Preparation Example 196 To a solution of 1.0 g of tert-butyl (3S)-piperidin-3-yl carbamate in 20 ml of DMF were added 0.77 ml of methyl 2-fluorobenzoate and 1.4 g of potassium carbonate, followed by stirring at 130° C. overnight. After leaving to be cooled, to the reaction mixture were added water and ethyl acetate to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 590 mg of methyl 2-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}benzoate.

The synthetic route of 394-35-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTELLAS PHARMA INC.; KOGA, Yuji; MAENO, Kyoichi; SATO, Ippei; IMAMURA, Yoshimasa; HANAZAWA, Takeshi; IIDA, Maiko; OHNE, Kazuhiko; IMAMURA, Kenichiro; WATANABE, Tsubasa; NOZAWA, Eisuke; SHIBATA, Hiroshi; US2014/88080; (2014); A1;,
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Electric Literature of 344-14-9, The chemical industry reduces the impact on the environment during synthesis 344-14-9, name is Dimethyl 2-fluoromalonate, I believe this compound will play a more active role in future production and life.

General procedure: A test tube chargedwith MS 3A (40.0 mg, 200 mg/mmol) was flame-dried under reduced pressure using a heat gun. After cooling to room temperature, argon was re-filled, Schiff base 1 (11.1 mg, 0.02 mmol), THF (0.2 mL) andGd(OiPr)3 (0.2 M THF solution, 0.1 mL, 0.02 mmol) were added. The mixture was stirred at roomtemperature for 30 min to afford yellow suspension. THF was, then, removed under reduced pressure. Tothe test tube were added Y(OTf)3 (10.7 mg, 0.02 mmol) and THF (0.20 mL), and the mixture was stirred at room temperature for 30 min to afford the Gd(OiPr)3/Y(OTf)3/Schiff base = 1:1:1 catalyst in THF.Then, DMAP (2.4 mg, 0.02 mmol) was added, and THF was removed under reduced pressure. After drying the residue under reduced pressure for 1 h at room temperature, toluene (0.2 mL) and Et2O (0.4mL) were added. To the resulting red suspension were added 2-fluoromalonate 3 (0.35 mmol, 1.7 equiv)and meso-aziridine 2 (0.20 mmol, 1.0 equiv), and the mixture was stirred for 17-72 h at 40 C. After themixture was cooled to room temperature and diluted with AcOEt, saturated EDTA?2Na aq. was added.The organic layer was separated, and the aqueous layer was extracted with AcOEt and the organic layers were washed with brine. The organic layers were dried over Na2SO4. After filtration and evaporation, the obtained crude mixture was purified by silica gel column chromatography (AcOEt/hexane/CH2Cl2) togive a corresponding product.

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

Reference:
Article; Fukagawa, Seiya; Xu, Yingjie; Anada, Masahiro; Yoshino, Tatsuhiko; Matsunaga, Shigeki; Heterocycles; vol. 94; 7; (2017); p. 1337 – 1350;,
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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. 1190-39-2, name is malonic acid dibutyl ester belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C11H20O4

Exemplary Synthesis 8 Method of Synthesis of Exemplary Compound 8 (0232) (0233) Intermediate 3 (16 g), dibutylmalonate (17 g), triethylamine (7.9 g) and acetonitrile (60 ml) were placed in a flask, and the content was stirred at 100 C. for 4 hours. Acetonitrile was removed, the residue was purified by column chromatography, and the eluate was recrystallized from ethanol to obtain a target product. The crystal was dried at 50 C. under air flow, to obtain 3.2 g of Exemplary Compound 8. (0234) lambdamax=370 nm (AcOEt) (0235) 1H-NMR (CDCl3) delta: 7.95 (d, 1H), 5.31 (d, 1H), 4.07 (s, 2H), 4.22 (s, 4H), 2.74 (s, 3H), 1.62-1.35 (m, 8H), 1.27 (s, 6H), 1.02 to 0.83 (m, 6H)

The synthetic route of 1190-39-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJIFILM CORPORATION; NORIZUKI, Yutaro; WATANABE, Yukie; TAKAHASHI, Kazutaka; (21 pag.)US2016/16919; (2016); A1;,
Ester – Wikipedia,
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Reference of 18013-97-3, 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. 18013-97-3 name is Diethyl 2,5-dibromoterephthalate, 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.

To a 100 mL dry three-necked flask with a magnetic rotor and a condenser, diethyl 2,5-dibromo-terephthalate (3.80 g, 10.0 mmol, 1.0 eq) was added sequentially.Phenylboronic acid (1.21 g, 10.0 mmol, 1.0 eq), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (570 mg, 0.5 mmol, 0.05 eq),Na2CO3 (2.12 g, 20 mmol, 2.0 eq).Nitrogen gas was distilled three times, then toluene (60.0 mL) and ethanol (20.0 mL) were added.Nitrogen gas was then bubbled for 20 minutes and the mixture was placed in a 90 C oil bath for 36 hours.The mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure.Eluent (petroleum ether / dichloromethane = 3: 1-1: 1) to give 3 as a white solid 256 mg, 7% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diethyl 2,5-dibromoterephthalate, and friends who are interested can also refer to it.

Reference:
Patent; Zhejiang University of Technology; Ruisheng Optoelectric Science And Technology (Changzhou) Co., Ltd.; Li Guijie; Lou Weiwei; Huang Da; Chen Shaohai; (46 pag.)CN109678906; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

110104-60-4, name is (E)-Methyl 4-chloro-3-methoxybut-2-enoate, 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. Safety of (E)-Methyl 4-chloro-3-methoxybut-2-enoate

A suspension of (S)-2-amino-3-cyclopentyl-propionic acid methyl ester hydrochloride (1.92 g, 9.13 mmol) in acetonitrile (18 mL) was treated with triethylamine (1.3 mL, 9.34 mmol). The mixture was then heated to 60 C., and kept at that temperature for 1 h. Then, additional triethylamine (1.3 mL, 9.34 mmol) was added followed by methyl-4-chloro-3-methoxy-(E)-2-butenoate (1367 mg, 8.30 mmol) in acetonitrile, via a syringe drop wise. The mixture was then heated to reflux by lowering into a pre-heated oil bath kept at 100 C. for 18 h, under nitrogen. The mixture was cooled to 25 C., and the precipitated triethylammonium hydrochloride was filtered off. The supernatant was concentrated and purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 120 g; 0% to 100% ethyl acetate/hexanes) to afford, (S)-3-cyclopentyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionic acid methyl ester (1.42 g, 58.2%) as light yellow oil: 1H NMR (DMSO-d6, 300 MHz) delta ppm 1.06 (m, 2 H), 1.36-1.90 (m, 9H), 3.61 (s, 3H), 3.77 (s, 3H), 3.94 (AB, Jgem=17.8 Hz, 2H), 4.62 (dd, J=4.8 Hz, 11.0 Hz, 1 H), 5.16 (s 1H).

The synthetic route of 110104-60-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Berthel, Steven Joseph; Brinkman, John A.; Hayden, Stuart; Haynes, Nancy-Ellen; Kester, Robert Francis; McDermott, Lee Apostle; Qian, Yimin; Sarabu, Ramakanth; Scott, Nathan Robert; Tilley, Jefferson Wright; US2009/264445; (2009); A1;,
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Ester – an overview | ScienceDirect Topics

Synthetic Route of 6065-82-3, These common heterocyclic compound, 6065-82-3, name is Ethyl diethoxyacetate, 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.

In a 250 mL round bottom flask, 9.5 mL of n-butyl lithium (2.5 M solution in hexane, 23.8 mmol) was added via a syringe to a pre-cooled solution (-78 C.) of 2-(2-methylbut-3-yn-2-yloxy)-tetrahydro-2H-pyran 2 (4.0 g, 23.8 mmol) in 100 mL of Et2O. The resulting solution was stirred for 30 min at -78 C., then ethyl 2,2-diethoxyacetate (4.9 g, 27.7 mmol) was added with a syringe, and the stirring continued for 12 hours. The reaction mixture was poured in an ice-cold saturated aqueous solution of NH4Cl. The aqueous layer was extracted with Et2O (3*50 mL). The organic solvent was separated with a separating funnel and dried with anhydrous MgSO4. The solvent was removed under reduced pressure and the resulting pale yellow oil was purified by radial chromatography (stationary phase silica gel, hexane/AcOEt 90:10) to provide 1,1-diethoxy-5-methyl-5-(tetrahydro-2H-pyran-2-yloxy)hex-3-yn-2-one 3 as a colorless liquid. Yield: 3.2 g (10.7 mmol; 45%). 1H-NMR in CDCl3 (delta, ppm): 5.05 (1H, q, J=5.0, 3.5 Hz, THP), 4.73 (1H, s, acetal), 3.92 (1H, m, THP), 3.69 (2H, m, CH2, acetal), 3.62 (2H, m, CH2, acetal), 3.50 (1H, m, THP), 1.82 (1H, m, THP), 1.71 (1H, m, THP), 1.58 (3H, s, CH3), 1.54 (3H, s, CH3), 1.52 (4H, m, THP), 1.25 (6H, t, J=7.0 Hz, CH3, acetal). 13C-NMR in CDCl3 (delta, ppm): 182.6, 101.1, 97.87, 96.10, 81.25, 70.57, 62.95, 62.64, 62.61, 31.47, 29.45, 28.85, 25.06, 19.92, 14.90 IR (neat, cm-1): 2978, 2937, 2872, 2214, 1687, 1074. HR ESIMS+ with acetonitrile as the mobile phase, (m/z): 299.1837 (M+, C16H26O5, 299.1853), 321.1660 (m/z) ([M+Na]+, C16H26O5Na, 321.1672).

Statistics shows that Ethyl diethoxyacetate is playing an increasingly important role. we look forward to future research findings about 6065-82-3.

Reference:
Patent; DUQUESNE UNIVERSITY OF THE HOLY GHOST; US2012/245168; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 14062-24-9,Some common heterocyclic compound, 14062-24-9, name is Ethyl 4-chlorophenylacetate, molecular formula is C10H11ClO2, 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: Sodium hydride (1.33 ml, 2.61 mmol) was added dropwise to a solution of phenyl acetonitrile (1.0 g, 8.5 mmol)) in anhydrous THF (30 mL), the mixture was stirred at R.T. for30 minutes, followed by adding a solution of ethyl 4-chlorobenzoate (1.78 g, 10.2 mmol) in anhydrous THF (30mL). The mixture was refluxed till the reaction was finished.The result mixture was quenched with water and extracted with ether. The aqueous layer was acidified with 10% HCl to filter out the white precipitation, which was recrystallized with ether to give a white solid. Yield: 76%-80%.

The synthetic route of 14062-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hu, Chunqi; Shen, Jianfeng; Du, Wenting; Letters in drug design and discovery; vol. 14; 2; (2017); p. 151 – 158;,
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Synthetic Route of 431-47-0, These common heterocyclic compound, 431-47-0, name is Methyl 2,2,2-trifluoroacetate, 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.

Synthesis of TFA-DOPA-OH (19)As seen in FIG. 2, step a, TFA-DOPA-OH (19) is synthesized by adding L-DOPA (39.4 g, 200 mmol), anhydrous MeOH (300 mL), and a magnetic stirring bar to a 1000 ml flask. The mixture was degassed with argon for 30 min, followed by addition of methyl trifluoroacetate (60 mL, 600 mmol) and triethylamine (112 mL, 800 mmol). The mixture was stirred at room temperature overnight. The volatile solvents were reduced by rotary evaporation and the residue was treated with 1 N HCl to a pH of ca. 1 and extracted with EtOAc. The organic layer was washed with 1N HCl and water, dried over MgSO4, and evaporated to give an off-white solid, 51.5 g (95%).

Statistics shows that Methyl 2,2,2-trifluoroacetate is playing an increasingly important role. we look forward to future research findings about 431-47-0.

Reference:
Patent; Northwestern University; US8227628; (2012); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics