Category: esters-buliding-blocks

Electric Literature of 141-12-8,Some common heterocyclic compound, 141-12-8, name is (Z)-3,7-Dimethylocta-2,6-dien-1-yl acetate, molecular formula is C12H20O2, 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: To a solution of the geranyl derivative (1.0 equiv) in acetonitrile(0.05 M) at 0 C, lithium bromide (2.0-2.4 equiv),4 A molecular sieves (1.0 mass equiv) and DIB (1.2-1.4 equiv) were added. After stirring for 5 min, the reaction mixture wasdiluted with EtOAc, filtered over alumina (EtOAc) and concentratedunder reduced pressure before purification by flash chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Z)-3,7-Dimethylocta-2,6-dien-1-yl acetate, its application will become more common.

Reference:
Article; Peilleron, Laure; Grayfer, Tatyana D.; Dubois, Joelle; Dodd, Robert H.; Cariou, Kevin; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 1103 – 1111;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

24812-90-6, name is Methyl 3-amino-4-methoxybenzoate, 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 3-amino-4-methoxybenzoate

Preparation of the compound of formula VII :; To a solution of METHYL-3-AMINO-4-METHOXYBENZOATE (a compound of FORMULA 11, AVAILABLE FROM INDOFINE CHEMICAL Company, INC., Somerset, New Jersey), (315 g, 1.74 mol) in 1 L MEOH, the crude enone VI (350 g,-2. 09 mol) was added. The reaction was stirred at room temperature for 30 minutes. After cooling to 0C for 1 hour, the solid was filtered and dried under vacuum to give the desired compound of formula Vil, methyl 4-methoxy-3- {[(E)-4-trifluoromethyl-3-oxo-1-butenyl] amino} benzoate, (500 g, 95% yield) as a yellow solid. 1H NMR (400 MHz, CDCI3) a 3.94 (s, 3H), 4.04 (s, 3H), 5.74 (d, J=8.0 Hz, 1H), 7.00 (d, J=8.8 Hz, 1H), 7.79 (dd, J=13. 2,8. 0 Hz, 1H), 7.87 (dd, J=8.8, 2.0 Hz, 1 H), 7.92 (d, J=2.0 Hz, 1 H), 11.01 (br, 1 H)

The synthetic route of 24812-90-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2005/28471; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

59247-47-1, name is tert-Butyl 4-bromobenzoate, 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. HPLC of Formula: C11H13BrO2

(2S,3’S)-2-Methyl-[1,3′]bipyrrolidinyl dihydrochloride (8) (1.1 g, 4 mmol) was treated with NaOt-Bu (1.1 g, 2equiv) in MeOH (30 mL), filtered, and concentrated. To this flask was added tert-butyl-4-bromo-benzoate (9) (1.0 g, 3.89 mmol), sodium tert-butoxide (538 mg, 5.6 mmol), tris(dibenzylideneacetone)-dipalladium-(0) (35 mg, 0.039 mmol), BINAP (72 mg, 0.116 mmol), and toluene (40 mL) under nitrogen. The reaction flask was heated to 80 °C (external) for 24 h with stirring until the starting material was completely consumed as judged by TLC analysis. The mixture was cooled to room temperature, taken up in DCM (50 mL), filtered, and concentrated. The crude product was then purified by a silica gel flash chromatography eluted with 0-5percent of 7 N NH3/MeOH in DCM to get 1.02 g (80percent) of the title compound as a yellow oil. LCMS: RT = 2.23 min, MS: 331 (M+H+). 1H NMR (300 MHz, CDCl3) delta 7.87 (d, J = 8.7 Hz, 2H), 6.49 (d, J = 8.7 Hz, 2H), 3.6-3.23 (m, 5H), 3.01 (m, 1H), 2.78 (m, 1H), 2.55 (q, J = 8.4 Hz, 1H), 2.22-1.43 (m, 13H), 1.14 (d, J = 6.3 Hz, 3H).

The synthetic route of 59247-47-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gao, Zhongli; Hurst, William J.; Hall, Daniel; Hartung, Ryan; Reynolds, William; Kang, Jiesheng; Nagorny, Raisa; Hendrix, James A.; George, Pascal G.; Bioorganic and Medicinal Chemistry; vol. 23; 3; (2015); p. 429 – 438;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 1459-93-4 as follows. Safety of Dimethyl isophthalate

In a round bottom flask was added dimethyl terephthalate, 0.07mol substituted and 150 mL of methanol, add 100mL of hydrazine hydrate, refluxed for 24 hours, cooled to room temperature for 5 hours and filtered, washed with water, and dried to give phthalimido-substituted hydrazide.

According to the analysis of related databases, 1459-93-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangxi Tianyuan biochemistry Co.Ltd; Zhang, Qing; Li, Weiguo; Li, Xianling; (15 pag.)CN103864711; (2016); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 394-35-4 as follows. name: Methyl 2-fluorobenzoate

0.06 mol of methyl o-fluorobenzoate,0.022 mol DIC,6.6 mmol DMAP was added to 100 mL dichloromethane, Stirring to continue stirring at room temperature for 30min,Gradually warming to 45 ~ 50 ,The reaction flask was charged with 1-cyclopropanecarbonylpiperazine (0.08 mol)Continue stirring reaction 9 ~ 10h.After the reaction is completed,Cool to 0 C and stir 45min,filter,The filtrate was washed with water (3 * 50 mL)Dried over anhydrous sodium sulfate,The methylene chloride was evaporated under reduced pressure,Got solid,Compound 2 (15.27 g),The yield is 92.57%.

According to the analysis of related databases, 394-35-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shandong Yuxin Pharmaceutical Co., Ltd.; Liu Zhenteng; Sun Yiwei; Li Zhen; Xu Guichao; Leng Xiangxiang; Huang Chunyan; (9 pag.)CN107266370; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 29263-94-3, 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 29263-94-3 as follows.

A. To a solution of 2-amino-5-nitrophenol (6.00 g, 0.0326 mol) in 80 mL of DMF was added diethyl 2-bromo-2-methyl malonate (6.2 mL, 0.0326 mol) and potassium fluoride (4.74 g, 0.0815 mol). The reaction mixture was heated at 60 C. for 6 hours. Water was added to quench the reaction and the reaction mixture was extracted with EtOAc. The combined organic fractions were dried over MgSO4, filtered and the filtrate was concentrated to dryness. The residue was purified by chromatography (silica with hexanes and ethyl acetate) to afford 2-methyl-6-nitro-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid ethyl ester.

According to the analysis of related databases, 29263-94-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Calvo, Raul R.; Cheung, Wing S.; Player, Mark R.; US2006/116368; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 27798-60-3, 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 27798-60-3 as follows.

Example 7a 3-(2,4-Dichloro-pyrimidin-5-yl)-2-(2-methoxy-phenyl)-propionic acid methyl ester To a solution of N-isopropylcyclohexylamine (1.44 g, 10.0 mmol) (Aldrich) in dry tetrahydrofuran (20 ML) was added n-butyllithium (2.5 M in hexanes, 4.0 ML, 10.0 mmol) (Aldrich) at -78 C. under argon.After 30 minutes, a solution of 2-methoxyphenylacetic acid methyl ester (1.8 g, 10.0 mmol) (TCI-US) in tetrahydrofuran (5 ML) was added by injection via a syringe and the reaction mixture was stirred at -78 C. for another 30 minutes.To the reaction mixture was added a solution of 2,4-dichloro-5-iodomethyl-pyrimidine (1.45 g, 5.0 mmol) (from Example 1c supra) in tetrahydrofuran (5 ML) at -78 C. and the reaction mixture was stirred at the same temperature for 1 hour then slowly allowed to warm up to -30 C. and stirred for 10 minutes.The reaction mixture was diluted with ethyl acetate (100 ML) and successively washed with saturated aqueous ammonium chloride solution (100 ML), water (50 ML) and brine (50 ML), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo.The residue was purified by flash column chromatography to give 3-(2,4-dichloro-pyrimidin-5-yl)-2-(2-methoxy-phenyl)-propionic acid methyl ester as a yellow oil. (Yield 1.40 g, 82.3%).

According to the analysis of related databases, 27798-60-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Liu, Jin-Jun; Luk, Kin-Chun; US2004/122029; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 34837-84-8, 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. 34837-84-8, name is Methyl 2-(4-fluorophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

5A. Methyl 2-(4-fluorophenyl)-3-(4-(methylsulphonyl)phenyl)-3-oxopropanoate A solution of methyl 2-(4-fluorophenyl)acetate (2.35 g, 14 mmol) in THF (15 mL), at -78° C., was treated dropwise with 1 N lithium bis(trimethylsilyl)amide (14 mL, 14 mmol). After 15 minutes a suspension of 4-(methylsulphonyl)benzoyl chloride (3.3 g, 15 mmol) in THF (25 mL) was added in portions. The reaction mixture was stirred for 60 minutes at -78° C. and at 0 to 5° C. for 12 hours. The mixture was quenched with 10percent citric acid, the THF removed in vacuo, and the residue triturated with hexanes to provide the desired product as a solid (yield: 3.4 g; 69percent). MS (DCI-NH3) m/z 368 (M+H)+; 1H NMR (300 MHz, DMSO-d6) delta3.27 (s, 3H), 3.69 (s, 3H), 6.35 (s, 1H), 7.21 (m, 2H), 7.44 (m, 2H), 8.06 (d, J=9 Hz, 2H), 8.25 (d, J=9 Hz, 2H).

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, Methyl 2-(4-fluorophenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Abbott Laboratories; US6472416; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, 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. name: Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate

To a solution of Preparation 232 1-hydroxymethyl-cyclopropanecarboxylic acid ethyl ester (3.00 g, 21.00 mmol) in dichloromethane (50 ml), at 0 C., was added saturated sodium hydrogen carbonate solution (50 ml), followed by TEMPO (659 mg, 4.00 mmol) and sodium bromide (400 mg, 4.00 mmol). After stirring for 5 min, sodium hypochlorite solution (10%, 14.00 mmol) was added slowly, followed by saturated sodium thiosulphate solution (50 ml). The two layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic phases were dried (MgSO4) and concentrated in vacuo to give the titled compound (3.00 g). 1H-NMR (CDCl3): 1.25-1.35 (3H), 1.55-1.64 (4H), 4.21-4.30 (2H), 10.39-10.41 (1H)

The synthetic route of 3697-68-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Billen, Denis; Boyle, Jessica; Critcher, Douglas James; Gethin, David Morris; Hall, Kim Thomas; Kyne, Graham Michael; US2006/287365; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 40876-98-0, 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. 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, This compound has unique chemical properties. The synthetic route is as follows.

5-Aminopyrazole (25 g) and diethyl oxalacetate sodium salt (74.4 g) were dissolved under cooling in 1 N hydrochloric acid. 68.75 ml_ of glacial acetic acid were added and the mixture was stirred at 80C for 14 h. The mixture was cooled to room temperature and the formed precipite was filtered off and titurated in ethyl acetate to give 16.06 g (26%) of the desired product.LC/MS (Method LC1 ): Rt = 0.86 min; m/z = 208.07 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SANOFI; Plettenburg, Oliver; Loehn, Matthias; Mendez-Perez, Maria; Hachtel, Stephanie; Podeschwa, Michael; Kannt, Aimo; Ivashchenko, Yuri; Bjergarde, Kirsten; WO2013/60636; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics