Month: May 2021

Reference of 4720-83-6, These common heterocyclic compound, 4720-83-6, name is 6-Oxabicyclo[3.2.1]oct-3-en-7-one, 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 6-oxabicyclo [3.2. 1] oct-3-en-7-one (2.6 g, 21 mmol) in xylenes (50 ml) under nitrogen was added benzylamine (3.42 g, 32 mmol). The mixture was heated under reflux for 16 h, then cooled to room temperature. The heavy white precipitate was collected by filtration, and recrystallized from dichloromethane/hexane to give the amide as a white solid (3.8 g, 78%, m. p. 127- 128C)

The synthetic route of 4720-83-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TARGACEPT, INC.; WO2005/37832; (2005); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 1268830-91-6, 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. 1268830-91-6 name is Methyl 3-amino-6-fluoro-2-methoxybenzoate, 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.

A 250 mL round bottom flask was charged with a solution of methyl 3-amino-6-fluoro-2-methoxybenzoate (3.656 g, 18.36 mmol) in methylene chloride (100 mL). A solution of 4-dimethylaminopyridine (113 mg, 0.925 mmol), pyridine (7.45 mL, 92.1 mmol) and propane- 1-sulfonyl chloride (8.25 mL, 73.6 mmol) in methylene chloride (10 mL) was added to the reaction mixture over the course of five minutes. The reaction mixture was stirred at room temperature for 14 hours. After removing the organic solvent under reduced pressure, saturated aqueous sodium bicarbonate (100 mL) was added followed by stirring for 10 minutes. The aqueous mixture was extracted twice with ethyl acetate (200 mL). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product was purified using flash chromatography, eluting with 0- 30% ethyl acetate/heptanes to give methyl 6-fluoro-2-methoxy-3-(propylsulfonamido)- benzoate as an oil (4.914 g, 85%). 1H NMR (400 MHz, (CD3)2SO) delta = 9.27 (s, 1H), 7.48 (dd, J=9.1, 6.1, 1H), 7.09 (t, J=9.0, 1H), 3.89 (s, 3H), 3.85 – 3.74 (m, 3H), 3.29 (s, 15H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-6-fluoro-2-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen; MATHIEU, Simon; MORENO, David; REN, Li; RUDOLPH, Joachim; WENGLOWSKY, Steven Mark; WO2012/118492; (2012); A1;,
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 89901-03-1 as follows. Computed Properties of C14H11BrO2

A solution of 4 -BROMO-BIPHENYL-4-CARBOXYLIC acid methyl ester, 7.8g (27.9 mmol) in 150ML of tetrahydrofuran was cooled to 0 C via ice-water bath. LITHIUMALUMINUM- hydride, L. lg (27.9 mmol) was added to the solution in one portion. The reaction mixture stirred at 0 C for LH. The mixture was slowly quenched with lOmL of isopropyl alcohol, then with lOmL of water. The aqueous mixture was extracted with 3X50ML portions of ethyl acetate. The organic layers were combined, washed with sat. aq. NaCl, and dried (MGSO4). The solution was concentrated to afford the desired product in 7. 01g (100%) as a white solid. The material was taken to the next step without further purification.

According to the analysis of related databases, 89901-03-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE INSTITUTE OF PHARMACEUTICAL DISCOVERY, LLC; WO2004/99170; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 53088-68-9, These common heterocyclic compound, 53088-68-9, name is Methyl (3-Chlorophenyl)acetate, 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.

EXAMPLE 96; Synthesis of (3-Chloro-phenyl)-[4-(7-methoxy-thiazolo[5,4-d]pyrimidin-2-ylcarbamoyl)-piperazin-1-yl]-acetic acid methyl ester; Step 1: A mixture of (3-Chloro-phenyl)-acetic acid methyl ester (2.0 g, 10.8 mmol), N-bromosuccinimide (1.95 g, 11.0 mmol) and 3 drops of hydrobromic acid (48% solution) in chloroform (100 mL) was heated under reflux for three days. Additional amounts of N-bromosuccinimide and hydrobromic acid were added to drive the reaction to completion. The reaction mixture was concentrated to dryness, taken up in methylene chloride and loaded onto a column of silica gel. Elution with 10% ethyl acetate/hexanes gave Bromo-(3-chloro-phenyl)-acetic acid methyl ester (1.95 g, 69% yield) as a colorless oil. The NMR spectrum obtained on the sample is compatible with its structure.

The synthetic route of 53088-68-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Brinkman, John A.; Cheung, Adrian Wai-Hing; Firooznia, Fariborz; Guertin, Kevin Richard; Marcopulos, Nicholas; Qi, Lida; Racha, Jagdish Kumar; Sarabu, Ramakanth; Tan, Jenny; Tilley, Jefferson Wright; US2007/270433; (2007); 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. 909563-22-0, name is Methyl 4-amino-2-isopropoxybenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 4-amino-2-isopropoxybenzoate

To a solution of methyl 4-amino-2-(propan-2-yloxy)benzoate (CAS Registry Number 909563-22-0) (2.33 g, 11.1 mmol) in ethyl acetate (25 mL), N-chlorosuccinimide (1.5 g, 11 mmol) was added, followed by heating at 50 C. After completion of the reaction, a residue obtained through concentration of the reaction solution under reduced pressure was purified by silica gel column chromatography [elution solvent: n-hexane/ethyl acetate=100/0-0/100 (V/V)] to obtain 2.7 g (quantitative yield) of the title compound in the form of a solid. (0297) MS m/z: 244, 246 (M+H)+.

The synthetic route of 909563-22-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; Soneda, Tsuyoshi; Sakai, Hiroki; Matsumoto, Koji; Tanaka, Naomi; Fukunaga, Taichi; (39 pag.)US2019/365688; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 66315-23-9, name is Ethyl 3-amino-4-(methylamino)benzoate, 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 66315-23-9, COA of Formula: C10H14N2O2

Step 1-1-4 Ethyl 1-methyl-1H-benzimidazole-5-carboxylate Ethyl 3-amino-4-methylaminobenzoate (24.1 g, 124 mmol) in the Step 1-1-3 was dissolved in formic acid (200 ml), and the solution was heated under reflux for 2 hours. After being cooled by ice, the solution was neutralized with a 25% ammonia water. The solution was subjected to extraction with chloroform, and the extract was dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (chloroform:methanol=20:1) to give the title compound (26.1 g, quantitative) as a light-purple powder. 1H-NMR (CDCl3) delta: 8.52 (d, J=1.5 Hz, 1H), 8.04 (dd, J=1.5, 8.5 Hz, 1H), 7.92 (s, 1H), 7.39 (d, J=8.5 Hz, 1H), 4.40 (q, J=7.3 Hz, 2H), 3.86 (s, 3H), 1.41 (t, J=7.3 Hz, 3H) Mass, m/z: 204 (M+), 159 (base)

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, Ethyl 3-amino-4-(methylamino)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Uchida, Hiroshi; Asagarasu, Akira; Matsui, Teruaki; US2013/79306; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 39552-81-3, 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 39552-81-3 as follows.

EXAMPLE 3 N-(4-Methoxycarbonylmethylphenyl)-L-glutamine: Compound (3) Following the procedure described in (a) of Example 1, 11.14 g (0.03 mole) of N-carbobenzoxy-L-glutamic acid alpha-benzyl ester was reacted with 4.96 g (0.03 mole) of methyl p-aminophenylacetate to give 13.38 g (88% yield) of an intermediate. The intermediate was dissolved in 500 ml of tetrahydrofuran, 200 ml of methanol and 100 ml of water. To the solution was added 0.5 g of palladium black and the mixture was subjected to hydrogenation at atmospheric pressure to give 6.09 g (79% yield) of N-(4-methoxycarbonylmethylphenyl)-L-glutamine, m.p. 183.3-184.2 C. [alpha]D25 =+29.2 (c=1 2 N HCl)

According to the analysis of related databases, 39552-81-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Chemical Industries Ltd.; Nippon Shinyaku Co., Ltd.; US4439448; (1984); 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. 2672-58-4, name is Trimethyl benzene-1,3,5-tricarboxylate, A new synthetic method of this compound is introduced below., Formula: C12H12O6

The acid chloride (43) was prepared as follows. Trimethyl-1 ,3,5-benzenetricarboxylate (46) was converted to the mono-acid diester (47) according to literature procedures (Dimick, et al. “On the Meaning of Affinity: Cluster Glycoside Effects and Concanavalin A” J. Am. Chem. Soc. 1999, 121 , 10286- 10296), and compound 47 was refluxed in excess thionyl chloride to give acid chloride 43 (Scheme 5).

The synthetic route of 2672-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARIZONA BOARD OF REGENTS, A BODY CORPORATE OF THE STATE OF ARIZONA, ACTING FOR AND ON BEHALF OF ARIZONA STATE UNIVERSITY; WAGNER, Carl E.; JURUTKA, Peter W.; MARSHALL, Pamela A.; VAN DER VAART, Arjan; WO2011/103321; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 33491-30-4, name is 8-Bromo-2H-chromen-2-one, 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 33491-30-4, Application In Synthesis of 8-Bromo-2H-chromen-2-one

General procedure: Under inert atmosphere (N2), in a 25 mL round bottom flask, Ar3Bi (0.208 mmol; 0.35 eq.), CsF (0.24 g: 1.8 mmol; 3 eq.), PPh3 (0.004 g: 0.018 mmol; 3 mol%), the aryl bromide (0.60 mmol; 1 eq.) was added to DMF (5 mL). The solution was warmed to 90 C prior addition of PEPPSI IPr (0.012 g: 0.018 mmol; 3 mol%). The reaction was monitored by GC/MS to follow the total consumption of the aryl bromide. Cooled to room temperature (RT), the reaction mixture was diluted by addition of diethyl ether (20 mL) and aqueous HCl 6 M (30 mL). After decantation, the aqueous solution was extracted with diethylether (2 * 20 mL). The collected organic phases were then washed with HCl 6 N (2 * 25 mL), water (25 mL) and brine (25 mL) prior drying over MgSO4. After concentration under reduced pressure, the resulting crude product was subjected to purification by column chromatography leading after concentration under reduced pressure to the title compound.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Cassirame, Benedicte; Condon, Sylvie; Pichon, Christophe; Journal of Molecular Catalysis A: Chemical; vol. 425; (2016); p. 94 – 102;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 18355-74-3,Some common heterocyclic compound, 18355-74-3, name is Methyl 2,3-difluorobenzoate, molecular formula is C8H6F2O2, 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.

[000113] To a stirred solution of compound 44 (800 mg, 4.65 mmol) in DMF (10 mL) under inert atmosphere were added (4-methoxyphenyl) methanethiol 8 (282 mg, 5.11 mmol), cesium carbonate (1.66 g, 5.11 mmol) at RT and stirred for 6 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was diluted water (25 mL) and extracted with ether (2 x 40 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 20% EtOAc/ hexanes to afford compound 45 (750 mg, 53%) as an off- white solid. TLC: 20% EtOAc/ hexanes (R 0.4); 1H NMR (DMSO-d6, 500 MHz): oe 7.49-7.36 (m, 3H), 7.10 (d, J= 8.9 Hz, 2H), 6.79 (d, J= 8.9 Hz, 2H), 4.06 (s, 2H), 3.81 (s, 3H), 3.70 (s, 3H);

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2,3-difluorobenzoate, its application will become more common.

Reference:
Patent; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; ASSEMBLY BIOSCIENCES, INC.; TURNER, William W.; ARNOLD, Lee Daniel; MAAG, Hans; ZLOTNICK, Adam; WO2015/138895; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics