Category: esters-buliding-blocks

Reference of 185312-82-7, The chemical industry reduces the impact on the environment during synthesis 185312-82-7, name is Methyl 4-bromo-2-chlorobenzoate, I believe this compound will play a more active role in future production and life.

Synthesis of methyl 3 -chloro-4?-(4,4-difluoropiperidine- 1 -carbonyl)biphenyl-4- carboxylate (46): Methyl 4-bromo-2-chlorobenzoate (45; 3.9 g, 15.7 mmol), (4,4- difluoropiperidin- 1 -yl)(4-(4,4, 5,5 -tetramethyl- 1,3 ,2-dioxaborol an-2-yl)phenyl)methanone (6.6 g, 18.8 mmol), Pd(dppf)C12 (2.29 g, 3.1 mmol), and K2C03 (6.48 g, 47 mmol) were added in a mixture of dioxane (60 mL) and water (6 mL) and degassed. The reaction mixture was heated at 100 C under nitrogen atmosphere for 2 h. The reaction mixture was cooled down to room temperature, filtered and the filtrate was concentrated under reduced pressure to give the crude product, which was purified by silica gel chromatography (20-50% EtOAc/petroleum ether) to yield 6.0 g of methyl 3 -chloro-4?-(4,4-difluoropiperidine- 1-carbonyl)biphenyl-4-carboxylate 46 as white solid (yield 97%). LCMS: m/z 394.0 [M+H], tR = 1.72 min

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 4-bromo-2-chlorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KARYOPHARM THERAPEUTICS INC.; BALOGLU, Erkan; SHACHAM, Sharon; SENAPEDIS, William; (153 pag.)WO2017/31213; (2017); 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. 3196-15-4, name is Methyl 2-bromobutyrate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C5H9BrO2

Example 11; Preparation of intermediate 2-(4-chloro-2-formyl-phenoxy)-butyric acid methyl ester; A mixture of 5-chloro-2-hydroxy-benzaldehyde (156 g, 1 mol), 2-bromo-butyric acid methyl ester (271 g, 1.5 mol), KI (2 g, 0.012 mol) and K2CO3 (276 g, 2 mol) in DMF (500 mL) was heated at 130 0C for 2 h. After cooled to room temperature, the mixture was concentrated. The residue was partitioned between EtOAc and water. The organic layer was washed with water, brine, dried over anhydrous Na2SO4 and concentrated to give the title compound (240 g).

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 3196-15-4.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; CHEN, Li; HAN, Xingchun; YANG, Song; ZHANG, Zhuming; WO2010/121995; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 5445-17-0, 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. 5445-17-0, name is Methyl 2-bromopropanoate, This compound has unique chemical properties. The synthetic route is as follows.

Example 7 methyl 2-(2-(pyrrolidin-1-yl)cyclohex-2-en-1-yl)propanoate To a 1 L round bottom flask was added 1-(cyclohex-1-en-1-yl)pyrrolidine (100 g, example 1), acetonitrile (800 mL), methyl 2-bromopropanoate (116.3 g), and sodium iodide (9.9 g). The mixture was then heated to reflux while stirring for 20 hours. The mixture was cooled to room temperature, added DBU (100.3 g), and stirred for 30 minutes. The resulted mixture was then concentrated to remove most acetonitrile, followed by addition of toluene (500 mL). The suspension was stirred at room temperature for 1 hour followed by filtration. The filter cake was washed with small amount of toluene twice. The combined toluene solution was distilled under vacuum to give a liquid product, 143.4 g (91.4%). 1HNMR (CDCl3): delta 4.64 (t, 1H), 3.60 (s, 3H), 2.99 (q, 2H), 2.73 (m, 2H), 2.56 (m, 2H), 2.05 (m, 1H), 1.97 (m, 1H), 1.73 (m, 5H), 1.54 (m, 3H), 1.01 (d, 3H).

The chemical industry reduces the impact on the environment during synthesis Methyl 2-bromopropanoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Yi, Lin; Su, Xiping; Werth, Peter; (16 pag.)US2016/326113; (2016); A1;,
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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. 125483-57-0, name is Benzyl 1-aminocyclobutanecarboxylate 4-methylbenzenesulfonate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

This compound (2.58 g; 0.00686 moles) was reacted with [(2S,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-(4-methylsulfonyl-phenyl)]-butanoic acid (2 g; 0.0049 moles) in a way similar to that described in example 1. A crude (2.9 g) was obtained and crystallized, first, from acetonitrile and, then, from ethanol giving 1[(2S,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-(4-methylsulfonyl-phenyl)-butanoyl]-amino-1-cyclobutanecarboxylic acid benzyl ester (1.74 g; 50% yield) as a white crystalline solid with m.p. 163-165 C. 1 H–NMR (200 MHz, CD3 OD-TMS): delta (ppm): 7.85-7.45 (m, 4H), 7.36-7.18 (m, 10H); nuA =5.15-nuB =5.11 (ABq, JAB =12.4 Hz, 2H); nuA =4.95-nuB =4.88 (ABq, JAB =12.6 Hz, 2H); 4.24 (m, 1H); 3.99 (d,1H, J=2.7 Hz); 3.06 (s, 3H); 3.08-2.84 (m, 2H); 2.68-2.46 (m, 2H); 2.35-2.15 (m, 2H); 2.04-1.84 (m, 2H).

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; Zambon Group, S.p.A.; US5145872; (1992); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 56741-34-5, 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. 56741-34-5, name is Methyl 5-amino-2-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of compound 11a (154 mg, 1.0 mmol) in anhydrous CH2Cl2 (10 mL) was added 3,5-dichlorobenzoyl chloride (209 mg, 1.0 mmol) and pyridine (241 mL 3.0 mmol) under ice bath. After stirring at room temperature for about 8 h, the solvent was removed in vacuum. The resulting residue was dissolved in NaOH (1 M) water solution (3 mL) and CH3OH (3 mL) and stirred for another 2 h. Then the solvent was removed under vacuum, and the residue was acidied to pH 2 or below with HCl (1 M) water solution. The solution was extracted with ethyl acetate twice and the combined organics were dried over anhydrous sodium sulfate and concentrated in vacuum. The resulting residue was puried by silica gel chromatography to give the desired compound as a white solid (234 mg, yield 85.0%)

The chemical industry reduces the impact on the environment during synthesis Methyl 5-amino-2-fluorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Gao, Ding-Ding; Dou, Hui-Xia; Su, Hai-Xia; Zhang, Ming-Ming; Wang, Ting; Liu, Qiu-Feng; Cai, Hai-Yan; Ding, Hai-Peng; Yang, Zhuo; Zhu, Wei-Liang; Xu, Ye-Chun; Wang, He-Yao; Li, Ying-Xia; European Journal of Medicinal Chemistry; vol. 154; (2018); p. 44 – 59;,
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Reference of 34529-06-1, The chemical industry reduces the impact on the environment during synthesis 34529-06-1, name is Dimethyl 3-aminophthalate, I believe this compound will play a more active role in future production and life.

5.43 2-(3-METHYL-2,6-DIOXOPIPERIDIN-3-YL)-4-PENTYLAMINO ISOINDOLE-1,3-DIONE Step 1: To a stirred solution of dimethyl 3-aminophthalate (0.84 g, 4.0 mmol) in CH2Cl2 (40 mL), was added pentanal (0.67 g, 8.0 mmol) and acetic acid (1.4 mL). The mixture was stirred for 5 minutes, followed by addition of sodium triacetoxyborohydride (2.5 g, 12 mmol). The mixture was stirred at ambient temperature overnight under an atmosphere of nitrogen. The reaction mixture was diluted with 60 mL of CH2Cl2, washed with water (2×100 mL), saturated aqueous sodium bicarbonate (2×100 mL) and brine (100 mL), and dried (MgSO4). The solvent was evaporated, providing 1.1 g of a light yellow oil.

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 3-aminophthalate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Muller, George W.; Chen, Roger Shen-Chu; Man, Hon-Wah; Ruchelman, Alexander L.; US2007/49618; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 1132-95-2, 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 1132-95-2 as follows.

The compound (103 mg) produced in production step 11-1 was dissolved in 2.0 mL of N,N-dimethylformamide. Cyclohexanone di-i-propyl acetal (58 muL) and 12.4 mg of p-toluenesulfonic acid were added to the solution, and the mixture was allowed to react at room temperature for one hr. A saturated aqueous sodium bicarbonate solution (20 mL) was added thereto, and the resultant precipitate was collected by filtration, was washed with water, and was dried under the reduced pressure to give the title compound (103 mg, 88%). Rf value: 0.53 (chloroform: methanol = 10: 1) ESIMS: m/z 1171 [M + Na]+

According to the analysis of related databases, 1132-95-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Meiji Seika Kaisha Ltd.; Microbial Chemistry Research Foundation; EP2036917; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. name: Methyl cyclopentanecarboxylate

Example 230 Preparation of 1-(3-Butenyl)cyclopentane Carboxylic Acid Methyl Ester To a solution of diisopropylamine (225 mmol, 31.6 mL) in THF (150 mL) was added dropwise a solution of n-butyl lithium (217.5 mmol, 87 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 (150 mmol, 19.23 g) in THF (30 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 4-bromo-1-butene (142.2 mmol, 19.2 g) in THF (30 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 (250 mL) and the mixture was extracted with ether (2*150 mL). The combined extracts were washed with a saturated solution of sodium chloride (150 mL) and dried over anhydrous magnesium sulfate. After filtration of the drying agent, the solution was concentrated under vacuum and the residue was distilled at 63-67 C./2.5 mm Hg to give 13.77 g (53%) of a colorless oil. HR MS (C11H16O2): Obs mass, 182.1311. Calcd mass, 182.1307 (M+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4630-80-2, its application will become more common.

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

Electric Literature of 6624-71-1,Some common heterocyclic compound, 6624-71-1, name is Dodecyl isobutyrate, molecular formula is C16H32O2, 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 I Dodecyl 3-hydroxy-2,2,3-trimethyl-4-oxopentanoate STR7 To a solution of diisopropylamine (5.56 g, 0.055 mole) in 200 ml of dry ether at 0 C. under nitrogen is added with stirring n-butyllithium (0.055 mole) in hexane (31 ml). The resulting mixture is cooled to -70 C., and a solution of dodecyl isobutyrate (12.8 g, 0.05 mole) in ether (25 ml) is added dropwise over a period of 20 minutes. The mixture is warmed to -15 C., and a solution of 2,3-butanedione (4.73 g, 0.055 mole) in ether (10 ml) is added rapidly. The mixture then is stirred at -5 C. for 15 minutes. The reaction mixture is combined with 200 ml of saturated ammonium chloride solution, and the separated organic layer is washed in sequence with 200 ml of 0.5N HCl, 200 ml of saturated sodium bicarbonate, and 200 ml of saturated sodium chloride. The solution is dried over magnesium sulfate and the solvent is removed under reduced pressure to give 19 g of an oil. The oil is distilled in a Kugelrohr apparatus (air bath temperature 85-115 C. at 0.1 mm Hg) to provide 13.5 g of almost pure product. Fractional distillation of the oil yields 11.5 g of pure product (67%), b.p. 132-133 C. at 0.05 mm Hg. IR and NMR data confirm the above structure. Anal. calc. for C20 H38 O4: C, 70.13; H, 11.18. Found: C, 70.11; H, 11.24.

The synthetic route of 6624-71-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Philip Morris Incorporated; US4701282; (1987); A;,
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 35180-01-9 as follows. Recommanded Product: Chloromethyl isopropyl carbonate

Step 1. Preparation of Iodomethylisopropyl carbonate: Tea solution of anhydrous sodium iodide (6 g, 40 mmol) in anhydrous acetonitrile (20 mL) chloromethyl isopropyl carbonate (2.9 g, 19 mmol) in anhydrous, acetonitrile (10 mL) was added drop wise over 20 min. The reaction mixture, covered with aluminum foil (protected from light) was stirred at room temperature overnight. The solid separated was filtered, washed with acetonitrile and the filtrate was concentrated under reduced pressure. Residue was dissolved in water (10 mL) and organics were extracted in ether (25 mL). Ether extracts were washed with sodium bisulfite (5%, 10 mL), later brine (10 mL). Organic layer was dried over anhydrous, sodium, sulfate, filtered, concentrated and dried under high dried vacuum. Yield 2.72 g (58%); 1H-NMR delta 1.3 (d, 6H), 4.95 (m, 1H), 5.95 (s, 2H).

According to the analysis of related databases, 35180-01-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SPRING BANK PHARMACEUTICALS, INC.; Iyer, Radhakrishnan P.; Coughlin, John Edward; (35 pag.)US2015/329864; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics