Category: esters-buliding-blocks

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. 145576-28-9, name is Ethyl 4-methylenecyclohexanecarboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C10H16O2

At 0 C, to a solution of ethyl 4-methylenecyclohexanecarboxylate (0.08 g) in DCE (1 mL) was added chloroiodomethane (0.110 mL, 1.522 mmol), followed bythe addition of 1 N diethylzinc in hexane (0.76 1 mL, 0.76 1 mmol). The reaction was stirred at 0 C for 1 hr, then stirred at rt for 18 hrs. The reaction mixture was diluted with EtOAc and 1 N HC1, the organic phase was washed with sat. NaC1, dried over anhydrous Na2SO4, filtered and concentrated. The crude product was charged to a 25 g silica gel cartridge which was eluted with a 20 mm gradient of 0-6% EtOAc inhexane to yield ethyl spiro[2.5]octane-6-carboxylate. ?H NMR (400 MHz, CDC13) ppm 4.08-4.18(2 H, m), 2.32 (1 H, tq, J=11.01, 3.53 Hz), 1.85 – 1.93 (2 H, m), 1.53- 1.74 (4 H, m), 1.28 – 1.35 (2 H, m), 1.22 – 1.28 (3 H, m), 0.28 (2 H, ddd, J=8.53, 5.52, 1.51 Hz), 0.17 – 0.25 (2 H, m).

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; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 5164-76-1, name is Dimethyl pent-2-enedioate, molecular formula is C7H10O4, 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. Application In Synthesis of Dimethyl pent-2-enedioate

General procedure: The crude aryl diazonium tosylate 9 thus obtained was dissolved or suspended in MeOH (30 mL). Dimethyl glutaconate (1.45 mL, 10.0 mmol) and Pd(OAc)2 (112 mg, 0.5 mmol) were successively added while stirring. After stirring at r.t. for 15 h, the mixture was concentrated under reduced pressure and partitioned between CH2Cl2 (40 mL) and H2O (25 mL). The organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was briefly fractionated on SiO2 using CH2Cl2 or CH2Cl2- acetone (5:1) as eluent. Fractions containing arylation product were pooled and concentrated to give compound 10 of at least 90% purity (according to 1H NMR analysis). It was used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5164-76-1, its application will become more common.

Reference:
Article; Dar’In, Dmitry; Kantin, Grigory; Bakulina, Olga; ?alubovskis, Raivis; Krasavin, Mikhail; Synthesis; vol. 51; 10; (2019); p. 2230 – 2236;,
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. 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H8BrNO2

A suspension of methyl 2-amino-5-bromobenzoate (460 mg, 2.0 mmol), potassium acetate (441 mg, 4.5 mmol) and pinacol diborane (1.52 g, 6.0 mmol) in 1,4-dioxane (20 mL) was degassed under a flow of N2 for 15 minutes. PdCb(dppf) (73 mg, 0.1 mmol) was added and the mixture heated to 95C for 16 hours. The reaction was deemed complete by LCMS. After cooling, the contents were partitioned between CH2C12 and water. The organic layer was washed with water, dried over anhydrous MgS04, filtered and evaporated. The product was purified by automated silica-gel chromatography eluting with a hexanes/EtOAc gradient. The fractions containing methyl 2- amino-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoate were concentrated to yield the product as a colorless oil = 560 mg (2.00 mmol, quant.). (0566) LC/MS – HPLC (254 nm) – Rt 3.32 min. MS (ESI) m/z 278.3 [M + H]+.

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; SIGNALRX PHARMACEUTICALS, INC.; MORALES, Guilermo, A.; GARLICH, Joseph, R.; DURDEN, Donald, L.; (166 pag.)WO2018/140730; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 185629-32-7, name is Methyl 4-amino-3-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8FNO2

To a 1L round-bottom flask was added methyl 4-amino-3-fluorobenzoate 30a (20 g, 118.24 mmol, 1.0 equiv.), AcOH (400 mL), and NaSCN (38.34 g, 473.33 mmol, 4.0 equiv.). The mixture was cooled at 0 C, and bromine (18.7 g, 117.01 mmol, 1.0 equiv) was added dropwise with stirring. The reaction mixture was stirred at 0 C for 2 hours, then at 30C for 3 days. 400 mL of water was added, the pH value of the solution was adjusted to 9 using sodium hydroxide. Solids were collected by filtration and dried in an oven under reduced pressure, to give 28 g (crude) of methyl 2-amino-4-fluoro-l,3-benzothiazole-6-carboxylate 30b as a yellow solid. The crude product was carried onto the next step without further purification.

According to the analysis of related databases, 185629-32-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; (231 pag.)WO2019/55808; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 609-08-5, 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. 609-08-5, name is Diethyl 2-methylmalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 6 Preparation of Diethyl 2-fluoro-2-methylmalonate Diethyl 2-methylmalonate (870 mg, 860 muL, 5 mmole) was dissolved in anhydrous tetrahydrofuran (10 mL) under nitrogen. Sodium hydride (250 mg as a 60% oil dispersion, 6 mmole) was added and the mixture was stirred until hydrogen evolution ceased (about 15 minutes). The reaction mixture was diluted with toluene (20 mL) and transferred dropwise to a solution of N-fluoro-N-neopentyl-p-toluenesulfonamide (1.295 g, 5 mmole) in anhydrous toluene (10 mL) over 5 minutes. A precipitate formed during addition and the reaction temperature rose from 23 to 36. After stirring an additional 5 minutes under nitrogen, the reaction mixture was diluted with ether (100 mL), washed with aqueous 1N oxalic acid (30 mL), 10% aqueous potassium bicarbonate (30 mL), and saturated aqueous sodium chloride (30 mL) solutions, and then dried over anhydrous magnesium sulfate. Filtration, removal of solvent under reduced pressure, and purification by flash column chromatography (silica, 1:1 methylene chloride-hexane) yielded diethyl 2-fluoro-2-methylmalonate (512 mg, 53% yield) as a colorless liquid. This material, and additional samples prepared by this procedure, were analyzed and provided the following results: IR (liquid film) gammamax (cm-1) 2940 (m), 1750 (s, ester), 1440 (m), 1370 (m), 1290 (s); 1 H NMR (80 MHz, CDCl3) delta1.33 (t, J=8 Hz, 6H, CH2 CHHD 3), 1.81 (d, J=22.67 Hz, 3H, CH3), 4.30 (q, J=8 Hz, 4H, CH2); 19 F NMR (94.1 MHz, CDCl3) -158.02 (q, J=22 Hz, 1F); HRMS (M–CH2 CH3) calcd. for C6 H8 O3 F: 147.0457; found: 147.0450; LRMS (CI) m/e 193.

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

Reference:
Patent; E. I. Du Pont de Nemours and Company; US4479901; (1984); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 18469-52-8, name is Methyl 4-(aminomethyl)benzoate, 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 18469-52-8, SDS of cas: 18469-52-8

(1) To a solution of methyl 4-(aminomethyl)benzoate (5.08 g) in methylene chloride (30 mL) was added di-tert-butyl dicarbonate (6.4 g) under ice-cooling and the mixture was stirred at room temperature for 24 hours. The reaction mixture was diluted with methylene chloride (20 mL) and thereto was added water (40 mL). After stirring, the organic layer was separated and concentrated in vacuo to give crude methyl 4-[N-(tert-butoxycarbonyl)aminomethyl] benzoate.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1772454; (2007); 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. 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl 2-ethoxy-2-iminoacetate

A mixture of 2-chloropyridine-3-sulfonamide (115) (50 mg, 0.26 mmol), ethyl 2-ethoxy-2- iminoacetate (56 mg, 0.39 mmol) and DBU (79 mg, 0.52 mmol) in ethanol (5 mL) was heated in a sealed tube at 130 C for 0.5 h then cooled to r.t.. The mixture was diluted with water (5 mL), adjusted to pH 5 with 1 M aqueous HCI and extracted with DCM (10 mL x 3). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by preparative TLC (MeOH/DCM = 1 :20) to give the product as a yellow solid (10 mg, 15% yield). LCMS (ES-API) Rt 0.51 min; m/z 256.1 [M+H]+. 1H NMR (400 MHz, d6-DMSO) 8.81 (dd, J = 4.8, 2.0 Hz, 1H), 8.43 (dd, J = 8.0, 1.6 Hz, 1H), 7.63 (dd, J = 8.0, 4.8 Hz, 1H), 4.41 (q, J = 7.2 Hz, 2H), 1.37 (t, J = 7.2 Hz, 3H).

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; CTXT PTY LIMITED; MORROW, Benjamin Joseph; FOITZIK, Richard Charles; CAMERINO, Michelle Ang; LAGIAKOS, Helen Rachel; WALKER, Scott Raymond; BOZIKIS, Ylva Elisabet Bergman; STEVENSON, Graeme Irvine; CUZZUPE, Anthony Nicholas; STUPPLE, Paul Anthony; (313 pag.)WO2019/43139; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 46193-76-4,Some common heterocyclic compound, 46193-76-4, name is Ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate, molecular formula is C9H9NO2S, 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) Preparation of thiophene pyrrole:Lipidothiophene pyrrole (1.95 g, 10 mmol)And potassium hydroxide (1 g, 18 mmol)Mixed in ethylene glycol (19.5 mL)Under inert gas protection and dark conditions, heated to 150 reaction 3h,After cooling to room temperature, add a large amount of distilled water to dilute,Extract with chloroform several times,Organic phase with water,Saturated sodium chloride solution,After drying, the solvent was removed by rotary evaporation,Quickly purified by silica gel column,Dichloromethane as eluent,Point before collecting components, dried to give thiophene pyrrole,Yield 85%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate, its application will become more common.

Reference:
Patent; Henan Normal University; Chang Yi; Niu Mengyuan; Liu Mengyang; (11 pag.)CN106905351; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 6627-89-0, name is tert-Butyl phenyl carbonate, This compound has unique chemical properties. The synthetic route is as follows., name: tert-Butyl phenyl carbonate

1-(t-butoxycarbonyl)indole can be prepared according to the procedure described: D. Dhanak, C. B. Reese J. Chem. Soc., Perkin Trans. 1 1986, 2181-2186: sodium hydride, in suspension in mineral oil, (0.77 g, 25.6 mmol) is washed twice with pentane then put into suspension in 10 mL of THF under a nitrogen atmosphere at ambient temperature. A solution of indole (1.01 g, 8.6 mmol) in 8.2 mL of THF is then added to this suspension. Once the reaction is completed (release of H2), t-butyl and phenyl carbonate (2.0 g, 10.25 mmol) are then added dropwise. The resulting reaction mixture is stirred for a further period of 12 hours at ambient temperature. 15 mL of water are then added, then the resulting mixture is extracted 3 times with ether. The organic phase obtained is dried over anhydrous MgSO4, filtered then evaporated under vacuum. The residue is purified by distillation (boiling point: 84 C./0.25 mm Hg) in order to produce 1.465 g (78%). The spectral characteristics are described in the publication.

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 6627-89-0.

Reference:
Patent; UNIVERSITE JOSEPH FOURIER; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; US2010/144726; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, molecular formula is C6H11NO3, 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. COA of Formula: C6H11NO3

(3) A mixture of ethyl 2-imino-2-ethoxyacetate (60 g) (purity 78.8%) and ammonium chloride (17.4 g) in methanol (180ml) was stirred for 3 hours at room temperature and cooled to -15 to -10 C. To the resulting mixture containing 1-methoxycarbonyl formamidine hydrochloride were dropwise added bromine (51.2 g) over a period of 10 minutes, triethylamine (71.1 g) over a period of 30 minutes and a solution of potassium thiocyanate (31.0 g) in methanol (150 ml) over a period of 30 minutes. The resulting mixture was stirred at -10 to -5 C. for 15 minutes and at 0 to 5 C. for an additional 1.5 hours. Precipitates were collected by filtration, washed with methanol and thereto was added cold water (200 ml). The mixture was stirred and the precipitates were collected by filtration, washed with cold water and dried to give methyl 5-amino-1,2,4-thiadiazole-3-carboxylate (32.5 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 816-27-3, its application will become more common.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US4425340; (1984); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics