Month: September 2021

Application of 756525-95-8, These common heterocyclic compound, 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, 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.

To a dried scintillation vial containing a magnetic stir bar was added tert-butyl 4-oxopiperidine-1-carboxylate (399 mg, 2 mmol), H2N-PEG2-COOt-Bu (550 mg, 2.4 mmol), 4 A molecular sieves (activated powder, 200 mg), and 1,2-dichloroethane (5 mL). The mixture was stirred for 1 h at room temperature. To the reaction mixture was added sodium triacetoxyborohydride (845 mg, 4 mmol). The mixture was stirred for 3 days at room temperature. The resulting mixture was partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 850 mg of compound 211 as a viscous oil. MS (ESI) mlz: [M+HjCalcd for C21H41N206 417.3; Found 417.2.

The synthetic route of 756525-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; R.P. SCHERER TECHNOLOGIES, LLC; RABUKA, David; MCFARLAND, Jesse M.; DRAKE, Penelope M.; BARFIELD, Robyn M.; (195 pag.)WO2017/83306; (2017); A1;,
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Ester – an overview | ScienceDirect Topics

Application of 816-27-3,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.

Sodium hydride (60% in oil, 0.390 g, 9.7 mmol) was added to a solution of 3-[tert- butyl(dimethyl)silyl]oxy-5-(3-fluoro-2-pyridyl)pyrrolidin-2-one (2.0 g, 6.4 mmol) in N,N- dimethylformamide (64 mL) at 0C. After 30 min, O-diphenylphosphorylhydroxylamine (2.3 g, 9.7 mmol) was added. The reaction was warmed to rt and stirred for 16h. The reaction was filtered and the filtrate was evaporated under reduced pressure. The crude residue was submitted to the next reaction without further purification. LCMS RT = 1.34 min, m/z = 326.0 [M + H]+ and LCMS RT = 1.30 min, m/z = 326.0 [M + H]+. Ethyl 2-ethoxy-2-iminoacetate (2.50 g, 16 mmol) and the crude residue were dissolved in ethanol (23 mL) and the reaction was heated at 90C for 16h. After cooling to rt, the reaction was filtered and the filtrate was concentrated under reduced pressure. The crude residue was submitted to the next reaction without further purification. LCMS RT = 1.38 min, m/z = 425.0 [M + H]+ and LCMS RT = 1.34 min, m/z = 425.0 [M + H]+. p-Toluenesulfonic acid monohydrate (1.5 g, 7.7 mmol) was added to a solution of the crude residue in toluene (25 mL). The reaction was heated at 120C for 16 h. After cooling to rt the reaction was filtered and the filtrate was concentrated under reduced pressure. The crude residue was submitted to the next reaction without further purification. LCMS RT = 1.55 min, m/z = 407.0 [M + H]+ and LCMS RT = 1.50 min, m/z = 407.1 [M + H]+. Tetrabutylammonium fluoride (1.0 M in THF, 6.4 mL, 6.4 mmol) was added to a solution of the crude residue in THF (21 mL) and the reaction was heated at 40C for 1 h. After cooling to rt saturated aqueous ammonium chloride was added. The aqueous layer was extracted with isopropyl acetate (4 x 50 mL). The combined organic layers were dried over sodium sulfate, concentrated and the crude residue was purified by flash column chromatography (silica 0% to 10% methanol/ dichloromethane) to give ethyl 5-(3-fluoro-2-pyridyl)-7-hydroxy-6,7-dihydro-5H- pyrrolo[l ,2-b] [l ,2,4]triazole-2-carboxylate (0.800 g, 2.74 mmol, 42% yield). NMR (400 MHz, Chloroform-if) 1 : 1 mixture of diastereomers delta 8.41 – 8.29 (m, 1H), 7.63 – 7.26 (m, 2H), 6.12 (dd, J = 8.1 , 4.4 Hz, 0.5H), 6.07 (d, J = 8.2 Hz, 0.5H), 5.64 (dd, J = 7.6, 4.0 Hz, 0.5H), 5.21 (d, J = 6.5 Hz, 0.5H), 4.51 – 4.38 (m, 2H), 3.45 (ddd, J = 14.7, 8.3, 6.6 Hz, 0.5H), 3.29 (ddd, J = 13.8, 7.5, 4.3 Hz, 0.5H), 3.10 (ddd, J = 13.8, 8.1 , 4.0 Hz, 0.5H), 2.74 (d, J = 14.4 Hz, 0.5H), 1.40 (t, J = 7.1 Hz, 3H). LCMS RT = 0.89 min, m/z = 292.9 [M + H]

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; HAMILTON, Gregory; ZHAO, Guiling; CHEN, Huifen; DANIELS, Blake; STIVALA, Craig; (358 pag.)WO2019/12063; (2019); 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

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

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 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;,
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. 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

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;,
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

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