Month: November 2020

653-92-9, name is Methyl 2-bromo-4-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. 653-92-9

Example 9A methyl 4-fluoro-2-phenoxybenzoate Methyl 2-bromo-4-fluorobenzoate (1 g), phenol (0.565 g), cesium carbonate (1.96 g), copper(I) triflate toluene complex (0.087 g), and ethyl acetate (0.034 mL) in toluene (12 mL) was stirred at 110 C. for 24 hours. The reaction was cooled and chromatographed on silica gel with 5% ethyl acetate/hexanes.

Statistics shows that 653-92-9 is playing an increasingly important role. we look forward to future research findings about Methyl 2-bromo-4-fluorobenzoate.

Reference:
Patent; ABBOTT LABORATORIES; US2010/184750; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

344-14-9, These common heterocyclic compound, 344-14-9, name is Dimethyl 2-fluoromalonate, 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.

First, put a stir bar in a 35 mL sealed tube, and then add methyl propargyl ether (28 muL, 0.33 mmol), 0.9 mL tetrahydrofuran (0.9 mL), and 2-chloroacetamidoquinoline (66.2 mg, 0.3 mmol), dimethyl 2-fluoromalonate (70.4 mg, 0.45 mmol). To the mixed solution were added CuI (5.7 mg, 0.03 mmol) and Cs2CO3 (117.3 mg, 0.36 mmol) in this order. The glass tube was filled with N2 for 3 minutes, the air was fully expelled, the nozzle was sealed with a cock, and the reaction was stirred at 800C for 1.5 hours. After the reaction was completed, the system was cooled to room temperature, 2 ml of distilled water was added to the reaction system, and ethyl acetate was used. After extraction, the organic phases were combined, and the solvent of the organic phase was distilled off under reduced pressure. 86.1 mg of the product was separated by silica gel column chromatography in 4d, and the yield was 71%.

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 344-14-9.

Reference:
Patent; Anyang Normal University; Lv Yunhe; Pu Weiya; Wang Xin; Wang Xiaoxing; (15 pag.)CN110627718; (2019); A;,
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. 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, A new synthetic method of this compound is introduced below., 252881-74-6

Compound 25 (50 mg, 40 mol), PyAOP (34 mg, 60 mumol) and DIPEA (15.2 muL, 160 mumol) were mixed in 2 mL of dry CH2Cl2 at rt. A portion of 7 (15 mg, 48 mumol) was then added and the resulting yellow solution was stirred for 4 h at rt. The crude reaction was washed with 0.01 N HCl (2¡Á10 mL), dried over Na2SO4, and concentrated. The benzyl-protected product was purified by preparative TLC (10% MeOH/CH2Cl2) and obtained as a white viscous solid (46 mg, 75%). TLC Rf=0.7 (10% MeOH/CH2Cl2). 1H NMR (CDCl3, 500 MHz) delta 1.42 (9H, s), 3.27-3.28 (2H, m), 3.50-3.52 (2H, m), 3.59-3.66 (12H, m), 4.02-4.07 (3H, m), 4.15-4.18 (3H, m), 4.90-4.94 (3H, m), 5.03-5.20 (12H, m), 7.10-7.45 (36H, m), 7.65-7.67 (2H, m), 7.85-7.85 (1H, m), 7.99 (1H, bs), 8.49-8.54 (3H, m) ppm. 13C NMR (CDCl3, 125 MHz) delta 28.3, 39.9, 40.2, 51.3, 51.4, 63.9, 64.1, 69.7, 70.0, 70.2, 70.3, 70.4, 71.1, 71.2, 76.2, 76.3, 79.0, 116.7, 117.5, 120.3, 123.0, 124.2, 125.4, 126.1, 126.2, 127.6, 127.6, 127.8, 128.2, 128.3, 128.4, 128.4, 128.4, 128.5, 128.6, 128.6, 128.7, 128.8, 128.8, 129.0, 130.2, 135.4, 135.7, 135.9, 135.9, 136.1, 146.8, 146.9, 149.0, 151.5, 151.8, 155.9, 164.2, 164.8, 164.9, 165.8, 168.9, 169.0, 169.1 ppm. HRMS (ESI): [M+Na]+ m/z calcd., 1550.5942. found, 1550.5977.

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; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; Nolan, Elizabeth Marie; Zheng, Tengfei; Chairatana, Phoom; US2015/105337; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

868-72-4, A common compound: 868-72-4, name is Dimethyl 2,5-dibromohexanedioate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Dimethyl 2,5-dibromoadipate (437 g) was added to DMF (4 L).Then, cesium carbonate (1 Kg) was slowly added thereto and heated to 120 C, and stirred for 36 hours.After the reaction is over, cool,Pour the reaction solution into 2L of ice water.Extraction with ethyl acetate (800 ml X3).The extracts were also combined, washed, dried and concentrated to give a crude material.Further recrystallization from n-hexane to obtainDimethyl 1,2-cyclobutanedicarboxylate(94g, yield 42%),

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 2,5-dibromohexanedioate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang Kaipu Chemical Co., Ltd.; Tan Xianghui; Luo Linfeng; Sun Yanping; Jia Junjian; Zhou Chen; (6 pag.)CN108658762; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

426-65-3, Name is Ethyl Pentafluoropropionate, 426-65-3, 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.

EXAMPLE 2 Potassium perfluoropropionate The procedure of Example 1 was followed using ethyl perfluoropropionate (4.8 g, 25 mmol), potassium trimethylsilanolate (3.2 g, 25 mmol), and dry ether (150 mL). Potassium perfluoropropionate (4.7 g, 93% yield) was isolated as a white solid: 19 F NMR (D2 O) delta -79.5 (m, CF3, 3F), -117.5 (m, CF2, 2F). Anal. Calcd. for C3 F5 KO2: C, 17.83; F, 47.00; K, 19.35. Found: C, 17.52; F, 46.83; K, 19.24.

Statistics shows that Ethyl Pentafluoropropionate is playing an increasingly important role. we look forward to future research findings about 426-65-3.

Reference:
Patent; E. I. Du Pont de Nemours and Company; US4723016; (1988); 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. 2318-25-4 name is Ethyl 3-ethoxy-3-iminopropionate hydrochloride, 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. 2318-25-4

(1-Ethoxyformimidoyl) 1-acetic acid ethyl ester hydrochloride (50g, 0.26mol) was suspended in an ammonia-ethanol solution (300mL; prepared by saturating ethanol with ammonia gas at room temperature), which was then stirred at room temperature for 4 hours. After the reaction was completed, the precipitated salt was removed by filtration, and the filtrate was concentrated in vacuo at room temperature to reach 1/3 of the amount. Hydrochloric acid-methanol (130mL; hydrochloric acid content:7.5percent) was added to this filtrate, the solution was then concentrated under a reduced pressure to obtain 3,3-diamino-acrylic acid ethyl ester hydrochloride (40g, 0.24mol, 92percent) as a solid. The resulting 3,3-diamino-acrylic acid ethyl ester hydrochloride (2.2g, 13.2mmol) was suspended in tetrahydrofuran (40mL), triethylamine (2mL, 14.3mmol) and acrylonitrile (1.2mL, 19.3mmol) were added thereto, and the solution was refluxed for 6 hours. After the reaction was completed, the resulting triethylamine hydrochloride was filtered, and the filtrate was concentrated to obtain the title compound (0.6g, 3.3mmol, 25percent). 1H-NMR Spectrum (CDCl3) delta(ppm) :1.26 (3H, t, J=7.2Hz), 2.42-2.49 (2H, m), 2.50-2.57 (2H, m), 4.12 (2H, q, J=7.2Hz), 4.22 (2H, brs), 6.45 (2H, brs).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3-ethoxy-3-iminopropionate hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Eisai Co., Ltd.; EP1669348; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

2435-36-1, These common heterocyclic compound, 2435-36-1, name is Dimethyl cyclopentane-1,3-dicarboxylate, 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.

Preparation of Bicyclic Amine Intermediate 3 (BAI-3) dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylateFreshly prepared lithium diisopropylamide (15 mL of n-butyllithium (2.5 M solution in hexane) and 5 mL of diisopropylamine were mixed at -30 C. in 50 mL of tetrahydrofuran) was cooled to -78 C. under nitrogen and stirred for 30 minutes. To a solution of dimethyl cyclopentane-1,3-dicarboxylate (2.67 g, 14.37 mmol) in tetrahydrofuran (12 mL) was drop added above freshly lithium diisopropylamide solution over 10 minutes (-75 C.-70 C.). The cold bath was then removed and the mixture was allowed to warm to 0 C. and maintained at that temperature for 20 minutes before being cooled to -80 C. A solution of 1-bromo-2-chloroethane (2 mL, 24 mmol) in tetrahydrofuran (25 mL) was added slowly to the reaction mixture over 35 minutes (-75 C.-70 C.). The reaction solution was then allowed to stir overnight with gradual warming to room temperature. The reaction was quenched by addition of saturated NH4Cl solution (20 mL). After removal of the solvent, 200 mL of ethyl acetate was added. The organic phase was washed with 2 N HCl (120 mL¡Á2), washed with brine and then dried over Na2SO4. After filtration and concentration, the residue was purified by chromatography on a silica gel column (eluted with ethyl acetate/petroleum ether=1/10) to afford the titled compound. 1H NMR (400 MHz, CDCl3), delta (ppm): 3.68 (s, 6H), 2.022.03 (m, 4H), 1.91 (s, 2H), 1.68 (s, 4H); LCMS (ESI+) m/z 213.1 (M+H)+.

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 2435-36-1.

Reference:
Patent; ABBOTT LABORATORIES; US2010/267738; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

104901-43-1,Some common heterocyclic compound, 104901-43-1, name is Methyl 3-bromo-4-methylbenzoate, molecular formula is C9H9BrO2, 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.

A pressure vessel was charged with methyl 3-bromo-4-methylbenzoate (5.0 g, 22 mmol), DMF (20 ml), water (1.25 ml) and tributylamine (8 ml, 34 mmol). Cesium acetate (2.1 g, 11 mmol) was then added and the flask was purged with N2. Palladium acetate (0.25 g, 1.0 mmol) and triphenylphosphine (2.9 g, 11 mmol) were added and the flask was purged with CO gas. The reaction mixture was then heated at 90 C. under 20 psi of CO gas with vigorous stirring overnight. The reaction mixture was diluted with 50 mL of toluene and extracted with saturated NaHCO3 (3*50 ml). The combined aqueous layer was washed with EtOAc (10 mL), then acidified using 2 N HCl to pH 5. The volume was reduced to about 50 mL and the resulting precipitate was collected by filtration, washed with water and dried to give 5-(methoxycarbonyl)-2-methylbenzoic acid as a white solid. MS (ESI, pos. ion) m/z: 193.1 (M-1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 104901-43-1, its application will become more common.

Reference:
Patent; Dimauro, Erin F.; Bemis, Jean E.; Chaffee, Stuart C.; Chen, Ning; Hu, Essu; Kunz, Roxanne; Martin, Matthew W.; McGowan, David C.; Rumfelt, Shannon; US2007/72862; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

5616-81-9, The chemical industry reduces the impact on the environment during synthesis 5616-81-9, name is tert-Butyl 2-(methylamino)acetate, I believe this compound will play a more active role in future production and life.

To a solution of methyl-4-formyl benzoate (2.0 g, 12.2 mmol) and sarcosine /er/-butyl ester (2.7 g, 14.6 mmol) in 1 ,2-dichloroethane (60 mL) was added 10 drops of glacial acetic acid followed by sodium triacetoxy borohydride (5.6 g, 26.8 mmol). The reaction mixture was heated to 60C and stirred at this temperature for 20 hours. The solution was poured into aqueous saturated NaHCO3 and extracted twice with EtOAc. The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo to afford 1.32 g of the desired product that was used without further purification: 1H NMR (400 MHz, cfe-DMSO) delta 7.91 (d, J= 8.0 Hz, 2H), 7.44 (d, J= 8.0 Hz, 2H), 3.83 (s, 3H), 3.69 (s, 2H), 3.18 (s, 2H), 2.23 (s, 3H), 1.42 (s, 9H); ESI+ MS: m/z (rel intensity) 294 (40, M+H).

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 2-(methylamino)acetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; METASTATIX, INC.; WO2008/109154; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common heterocyclic compound, 35180-01-9, name is Chloromethyl isopropyl carbonate, molecular formula is C5H9ClO3, 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. 35180-01-9.

2-butyl-4-chloro-1-[2′-(1H-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazole-5-carbo xylic acid (prepared by the method disclosed in) was reacted with trityl chloride to obtain 2-butyl-4-chcloro-1-[2′-(1-triphenylmethyl-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazol e-5-carboxylic acid. To a 100 ml of one-necked flask, 0,523 g of 2-butyl-4-chloro-1-[2′-(1-triphenylmethyl-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazol e-5-carboxylic acid, 0 124 g of potassium carbonate, and 5 ml of N,N-dimethylacetamide were added in turn The solution was stirred at the room temperature for 20 minutes. Then 0.562 g of 1-chloromethyl isopropyl carbonate was added and the mixture was reacted at 45 – 50 C for 16 h. After the reaction was completed, the mixture solution was filtered, and 30 ml of water was added into the filtrate. The resulting mixture was extracted with 30 ml of ethyl acetate twice. The organic phase was dried and concentrated to give 1.724 g of oil, which was directly used in the next reaction without purification

The synthetic route of Chloromethyl isopropyl carbonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHANGHAI ALLIST PHARMACEUTICAL., INC.; EP2103610; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics