Month: February 2021

Reference of 53518-15-3, A common heterocyclic compound, 53518-15-3, name is 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one, molecular formula is C10H6F3NO2, 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.

General procedure: A mixture of 7-aminocoumarin (500 mg, 12-16) and DMAP (10-20 mg) was dissolved in minimum amount of THF. To this acetic anhydride was added and the resultant mixture was stirred at room temperature for 24 h. On completion of the reaction 50 mL ice cold water was added. The crude off-white solid was then filtered, washed with water and dried. The crude solid so obtained was crystallized with ethanol to give 7-N-acetylaminocoumarin derivatives.

The synthetic route of 53518-15-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kathuria, Abha; Priya, Nivedita; Chand, Karam; Singh, Prabhjot; Gupta, Anjali; Jalal, Sarah; Gupta, Shilpi; Raj, Hanumantharao G.; Sharma, Sunil K.; Bioorganic and Medicinal Chemistry; vol. 20; 4; (2012); p. 1624 – 1638;,
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Electric Literature of 478375-40-5,Some common heterocyclic compound, 478375-40-5, name is Methyl 3-bromo-5-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.

Azobisisobutyronitrile (1.79 g) was added to methyl3-bromo-5-methylbenzoate (50 g)10 and N-bromosuccinimide (44.7 g) in 350 mL acetonitrile, and the mixture was refluxed overnight.An additional II g of N-bromosuccinimide and 0.5 g of azobisisobutyronitrile was added, and therefluxing was continued for 3 hours. The mixture was concentrated, taken up in 500 mL diethylether, and stirred for 30 minutes. The mixture was filtered, and the resulting solution wasconcentrated. The crude product was chromatographed on silica gel using 10% ethyl acetate in15 heptanes to give the title compound

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-bromo-5-methylbenzoate, its application will become more common.

Reference:
Patent; ABBVIE INC.; BOGHAERT, Erwin, R.; SOUERS, Andrew, J.; PHILLIPS, Andrew, C.; JUDD, Andrew, S.; BRUNCKO, Milan; (717 pag.)WO2017/214282; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 27741-65-7, name is Ethyl 2-cyclobutylideneacetate, 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 27741-65-7, Application In Synthesis of Ethyl 2-cyclobutylideneacetate

Step 2: 6′-Hydroxy-5,7′-dimethylspiro[cyclobutane-1,2′-thiochromen]-4′(3’H)-one To a solution of 4-mercapto-2,6-dimethylphenol (2.5 g) in anhydrous methanol (40 mL) containing trimethyl orthoformate (3 mL), was added cyclobutylidene-acetic acid ethyl ester (7.6 g) and then 5 drops of concentrated sulfuric acid. The solution was deoxygenated by bubbling with nitrogen, and was allowed to reflux for 4 days. The mixture was concentrated, washed with saturated NaHCO3 and extracted with ethyl acetate. After concentrated in vacuo, the residue was purified by flash chromatography eluted with 10-20% ethyl acetate in hexane to give 3.1 g of methyl {1-[(4-hydroxy-3,5-dimethylphenyl)thio]cyclobutyl}acetate as a white solid. The above addition product (3.1 g) was suspended in 200 mL of 1N NaOH in MeOH and water (1:1, v/v), and the mixture was allowed to stir for 1 hour. The reaction mixture was then acidified with 1N HCl and extracted 3 times with ethyl acetate. The organic layer was washed with water and dried over anhydrous Na2SO4, and concentrated in vacuo.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-cyclobutylideneacetate, and friends who are interested can also refer to it.

Reference:
Patent; Galileo Pharmaceuticals, Inc.; US2006/128790; (2006); 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. 10047-10-6, name is Methyl 2-aminopentanoate hydrochloride, A new synthetic method of this compound is introduced below., COA of Formula: C6H14ClNO2

(a) To a stirred solution of 7.36 ml (84.9 mmol) of chlorosulfonyl isocyanate in 150 ml of methylene chloride was added benzyl alcohol (8.82 ml, 84.7 mmol) at 0-5 C. After stirring the above solution for 1.5 hours at this temperature, a solution of 15.62 g (93.25 mmol) of 2-amino-pentanoic acid methyl ester hydrochloride in 500 ml of methylene chloride containing triethylamine (25.54 g, 0.2528 mol) was added at 0-5 C., and the resulting mixture was stirred overnight allowing the mixture to warm to room temperature. The reaction mixture was poured into 600 ml of 10% aq. HCl solution, saturated with sodium chloride, and the organic layer was separated. The aqueous layer was extracted with methylene chloride/ethyl acetate (4:1, 2*200 ml) and the combined organic layer was washed with brine, dried and concentrated in vacuo to yield 28.2 g (87.6%) of 2-(N-carbobenzyloxyaminosulfonyl) aminopentanoic acid methyl ester (Formula XIV: R=CH3, R1 =H; R2 =propyl; R3 =H) as a solid, m.p. 76-78 C.

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; Sterling Winthrop Inc.; US5494925; (1996); A;,
Ester – Wikipedia,
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Application of 252881-74-6,Some common heterocyclic compound, 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, molecular formula is C13H27NO5, 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.

[0075] 4-pentynoic acid was treated with t-Boc protected PEG amine (3) to give compound 11 and deprotected using TFA to afford compound 12, followed by activation using NHS to form its activated ester compound 13. The dendrimer was fully functionalized by amidation of a generation 1 dendrimer bearing a cleavable cystamine core (DNT-294, from Dendritic Nanotechnologies, Inc.) to generate compound 14 leaving a terminal alkyne for orthoganol conjugation through a click reaction. Compound 14 was isolated by preparative HPLC. The purity of 14 was confirmed by LC/MS deconvolution and MALDI analysis.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, its application will become more common.

Reference:
Patent; THE RESEARCH FOUNDATION FOR THE STATE UNIVERSITY OF NEW YORK; OJIMA, Iwao; WANG, Tao; TENG, Yu-Han; WO2015/38493; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 99548-54-6, 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. 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 106A Methyl 6-amino-3-bromo-2-methylbenzoate A -20 C. solution of methyl 3-bromo-2-methylbenzoate (10 g, 43.7 mmol) in concentrated H2SO4 (100 mL) was treated dropwise with a solution of concentrated HNO3 (2.75 muL) in concentrated H2SO4 (50 mL) at a rate that maintained the temperature below -15 C. The reaction was then stirred at 0 C. for 30 minutes, poured into ice, and extracted with diethyl ether. The extract was washed with aqueous NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated to give 9.32 g of the nitrated product. The crude product was added to a solution of SnCl2 (32.2 g, 170 mmol) in concentrated HCl (34 mL) and methanol (52 mL) and the resulting suspension was stirred at room temperature for 4 hours. The resulting solution was concentrated, adjusted to pH 7 with aqueous NaOH, and filtered through diatomaceous earth (Celite). The pad was washed with diethyl ether and dichloromethane and the combined filtrates were concentrated. The concentrate was purified by silica gel chromatography with 10-20% ethyl acetate/hexanes to give 3.59 g of the desired product. MS (ESI(-)) m/e 243 (M-H)-.

The synthetic route of Methyl 3-bromo-2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Curtin, Michael L.; Davidsen, Steven K.; Frey, Robin R.; Heyman, Howard R.; Holms, James H.; Michaelides, Michael; Steinman, Douglas H.; US2005/26976; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 57381-62-1, The chemical industry reduces the impact on the environment during synthesis 57381-62-1, name is Methyl 2-bromo-4-chlorobenzoate, I believe this compound will play a more active role in future production and life.

(4-Dibenzofuranyl) boronic acid ((4-dibenzofuranyl) boronic acid), 30 g (141.5 mmol), methyl-2-bromo-4-chlorobenzoate (methyl-2-bromo-5-chlorobenzoate), 37.1 g ( 148.6 mmol), tetrakistriphenylphosphine palladium 8.2 g (7.1 mmol) dissolved in toluene 550 ml was added to flask placed in a nitrogen atmosphere. Potassium carbonate (potassium carbonate) 104.2 g (707.51 mmol) was dissolved in 550 ml toluene, and the aqueous solution 353.8 ml was stirred under reflux for 12 hours. After completion of the reaction, the mixture was extracted with ethyl acetate, dried with magnesium sulfite (magnesium sulphate), filtered and the filtrate was concentrated under reduced pressure. The resulting mixture was purified by silica gel column chromatography using n-hexane / dichloromethane (7:3 volume ratio) to give the desired compound of intermediate (D) 38.2 g (80percent yield) as a white solid.

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

Reference:
Patent; CHEIL INDUSTRIES INC.; JO, YOUNG KYOUNG; KANG, EUI SU; KIM, DONG YEONG; LUI, JIN HYUN; MIN, SOO HYUN; YANG, YONG TAK; OH, JAE JIN; YU, EUN SUN; LEE, HAN ILL; JUNG, HO KUK; (42 pag.)KR2015/45809; (2015); 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. 136333-97-6, name is Methyl 4-(2-bromoethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 4-(2-bromoethyl)benzoate

Example 4A Diallyl 2-[4-(methoxycarbonyl)phenyl]ethylmalonate Under argon and at 0 C., 4.44 g (111.0 mmol) of sodium hydride (60% strength dispersion in mineral oil) are added a little at a time to a solution of 27.28 g (148.09 mmol) of diallyl malonate in 220 ml of anhydrous dioxane. The mixture is stirred at 40 C. for 30 min, and a solution of 18.00 g (74.04 mmol) of methyl 4-(2-bromoethyl)benzoate is then added at room temperature. The reaction mixture is then heated at 110 C. for 16 hours. After addition of 25 ml of saturated ammonium chloride solution, most of the dioxane is removed on a rotary evaporator. The residue is taken up in 200 ml of ethyl acetate and 100 ml of water. The aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After distillative removal of a large proportion of the excess diallyl malonate, the crude product is pre-purified on 100 g of silica gel 60 (mobile phase: cyclohexane/dichloromethane 2:1, then cyclohexane/ethyl acetate 4:1). The desired product is then isolated by preparative HPLC. This gives 11.60 g (22% of theory) of a colorless oil. LC-MS (method 2): Rt=2.53 min; MS (ESIpos): m/z=347 [M+H]+. 1H-NMR (400 MHz, CDCl3): delta=2.26 (m, 2H), 2.73 (t, 2H), 3.40 (t, 1H), 3.91 (s, 3H), 4.63 (d, 4H), 5.25 (d, 2H), 5.33 (d, 2H), 5.90 (m, 2H), 7.25 (d, 2H), 7.96 (d, 2H).

According to the analysis of related databases, 136333-97-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER HEALTHCARE AG; US2009/286882; (2009); 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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, A new synthetic method of this compound is introduced below., Recommanded Product: 924-99-2

6.1.1 Ethyl 2-(2,4-difluorobenzoyl)-3-(dimethylamino)acrylate (8) A mixture of substituted 2, 4-difluorobenzoyl chloride (3.19 g, 18.1 mmol), ethyl 3-(dimethylamino)acrylate (2.59 g, 18.1 mmol, 1.0 equiv), and triethylamine (2.74 g, 27.1 mmol, 1.5 equiv) in toluene (30 mL) was stirred at 90 C for 4 h. After cooling, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 2:1 to 1:2, v/v) to give the desired product 8 as yellow oil. Yield 65%; 1H NMR (400 MHz, CDCl3) delta 7.79 (s, 1H), 7.62-7.68 (m, 1H), 6.89-6.93 (m, 1H), 6.74-6.80 (m, 1H), 4.03-3.98 (q, J = 7.2 Hz, 2H), 3.31 (s, 3H), 2.89 (s, 3H), 0.95-0.99 (t, J = 7.2 Hz, 3H).

The synthetic route of 924-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mao, Tian-Qi; He, Qiu-Qin; Wan, Zheng-Yong; Chen, Wen-Xue; Chen, Fen-Er; Tang, Gang-Feng; De Clercq, Erik; Daelemans, Dirk; Pannecouque, Christophe; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3860 – 3868;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 35450-37-4, A common heterocyclic compound, 35450-37-4, name is Methyl 3-bromo-4-methoxybenzoate, molecular formula is C9H9BrO3, 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.

methyl 4′- (2-ethoxyethoxy)-6-methoxy-2′, 6′-dimethylbiphenyl-3- carboxylate A mixture of methyl 3-bromo-4-methoxybenzoate (0.90 g, 3.67 mmol), [4- (2-ethoxyethoxy)-2, 6-dimethylphenyl] boronic acid (0.87 g, 3.67 mmol), tris (dibenzylideneacetone) dipalladium (0) (0.13 g, 0.15 mmol), 2- (dicyclohexylphosphino) biphenyl (79 mg, 0.22 mmol), tripotassium phosphate (1.56 g, 7.34 mmol) and toluene (20 mL) was stirred under a nitrogen atmosphere at 90C for 18 hrs. The reaction mixture was cooled and insoluble material was filtered off. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-hexane/ethyl acetate=1/1) to give the title compound (0.71 g, yield 54%) as a yellow oil. MS (ESI+): 359 (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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/63729; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics