Month: June 2021

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. 51760-21-5, name is Dimethyl 5-bromoisophthalate, A new synthetic method of this compound is introduced below., Application In Synthesis of Dimethyl 5-bromoisophthalate

Into a round-bottom flask were charged with dimethyl 5-bromoisophthalate (0.50 g, 1.8 mmol), barium hydroxide octahydrate (0.43 g, 1.4 mmol) and methanol (10 mL). The mixture was stirred at room temperature overnight. HCl (2 N ethyl ether solution, 10 mL) was added and the volatiles were removed under reduced pressure. The residue was purified via flash chromatography to afford the desired product as a white solid. 1H NMR (400 MHz, DMSO-d6): 13.70 (br, IH), 8.42 (t, J = 1.5 Hz, IH), 8.31- 8.24 (m, 2H), 3.90 (s, 3H).

The synthetic route of 51760-21-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RENOVIS, INC.; WO2009/110985; (2009); A2;,
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. 105-53-3, name is Diethyl malonate, A new synthetic method of this compound is introduced below., Quality Control of Diethyl malonate

(a) Isobutyldiethyl malonate Diethyl malonate is treated with an ethanol and sodium ethoxide mixture. Then iso-butyl bromide is added to form isobutyl diethyl malonate as the product of this malonic ester synthesis.

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; E. R. Squibb & Sons, Inc.; US4382081; (1983); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 53518-15-3, 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 53518-15-3 as follows.

The Schiff base was synthesized from the condensation reaction between 7-amino-4-(trifluoromethyl)coumarin (0.2684g; 1.171mmol) and 20 2-amino-3-formylchromone (0.2216g; 1.171mmol) in 16 methanol (20cm3) which was heated under reflux for 3h. The resultant yellow solution was allowed to cool to room temperature before the light yellow precipitate was filtered and washed using cold methanol and 21 petroleum ether. Yield=50%; Melting point: 239.9-244.8C; Infrared (vmax/cm-1): nu(N-H) 3242, 3093 (br), nu(C=O) 1679 (s), nu(C=N) 1610 (s), nu(C-O-C) 1334 (s); 1H NMR (d6-DMSO/298K/ppm): 10.09 (s, 1H, H11), 9.59 (s, 2H, NH2), 8.05-8.01 (dd, J=7.7Hz, J=1.7Hz, 1H, H15), 7.76-7.70 (t, J=1.5Hz, J=1.1Hz, 3H, H17), 7.48-7.33 (m, 3H, H8, H16, H18), 6.68-6.64 (dd, J=8.8Hz, J=2.2Hz, 1H, H9), 6.53-6.50 (d, J=2.2Hz, 1H, H6), 6.43 (s, 1H, H3); 13C NMR (d6-DMSO/295K/ppm): 188.42 (C13), 175.58 (C20), 165.96 (C4), 159.86 (C19), 157.05 (C2), 154.57 (C11), 153.60 (C5), 134.59 (C7), 126.22 (C9), 126.20 (C14), 125.83 (C16), 125.70 (C1), 122.70 (C17), 117.34 (C15), 112.69 (C18), 107.92 (C10), 107.86 (C8), 102.23 (C6), 99.46 (C3), 99.14 (C12); UV-Vis (Methanol, lambdamax (epsilon, M-1cm-1)): 377nm (1361), 292nm (1297), 264nm (1785), 234nm (2698); TOF-MS (m/z): Calcd: 400.0671, Found: 400.0753 [M]+, 401.0750 [M+H]+, 402.0785 [M+2H]+.

According to the analysis of related databases, 53518-15-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jadoo, Barushka; Booysen, Irvin Noel; Akerman, Matthew Piers; Rhyman, Lydia; Ramasami, Ponnadurai; Polyhedron; vol. 144; (2018); p. 107 – 118;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 18595-14-7, name is Methyl 4-amino-3-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: esters-buliding-blocks

TEA (1.2 mmol) and the commercially available benzoyl chloride (1.1 mmol) wereadded at 000 to a solution of the corresponding aniline (1 mmol) in DCM (0.16M). The reaction mixture was left stirring at room temperature for 2h. Sat. solution of NaHCO3 (500m1) was added. The phases were separated and the aqueous layer was extracted with DCM (3 times). The combined organic layers were evaporated and purified by flash chromatography eluting with DCM/EtOAc to obtain the compounds of examples16-18,20,21 reported in Table 4.

The synthetic route of 18595-14-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROTTAPHARM BIOTECH S.R.L.; ARTUSI, Roberto; CASELLI, Gianfranco; ROVATI, Lucio; (78 pag.)WO2016/146220; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 89-91-8, 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. 89-91-8 name is Methyl 2,2-dimethoxyacetate, 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.

STR12 A mixture of methyl dimethoxyacetate (1) (8 mL, 65.5 mmol), glyoxylic acid monohydrate (5.8 g, 63 mmol) and p-toluenesulfonic acid monohydrate (60 mg, 0.32 mmol) was heated at 80 C. for 18 h. The resulting solution was cooled to 0 C. and phosphorus pentoxide (7.0 g, 49.3 mmol) was added. After heating for 4 h at 80 C., methyl glyoxylate (2) (7.9 g, 90 mmol) was obtained by distillation in 70% yield.

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

Reference:
Patent; Akzo Nobel, N.V.; US6150548; (2000); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 14920-81-1, name is Methyl 2,6-dimethylbenzoate, molecular formula is C10H12O2, 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 2,6-dimethylbenzoate

General procedure: To a flame-dried 250 mL round-bottom flask under argon wereadded 4 (8.02 g, 28.4 mmol, 1 equiv), TMEDA (8.71 mL, 58.2mmol, 2.05 equiv), and anhydrous n-hexane (28 mL). Theresulting solution was cooled in an ice bath and sec-butyllithium(1.4 M solution in cyclohexane, 42.0 mL, 58.2 mmol, 2.05equiv) was added dropwise. The ice bath was removed and thereaction mixture was stirred at room temperature for 4 h. Thereaction was cooled to -78 C and a solution of methyl 2,4,6-trimethylbenzoate (5.11 g, 28.7 mmol, 1.01 equiv) in anhydrousn-hexane (28 mL) was added slowly via cannula. After the addition,the mixture was allowed to slowly warm to room temperatureand stirred for 12 h. The reaction was quenched with water(25 mL) and the biphasic mixture was stirred vigorously for 30min. The mixture was diluted with Et2O (100 mL) and the layerswere separated. The organic layer was washed with water(2 × 150 mL) and brine (1 × 150 mL). The organic layer wastransferred to a 250 mL round-bottom flask equipped with astir bar. To the vigorously stirred solution was added conc. HCl(12 mL), resulting in a bright-yellow precipitate. The suspensionwas stirred vigorously for 30 min then diluted with water (150mL). The layers were separated and the organic layer wasextracted with water (3 × 150 mL or until the washings becomecolorless). To the combined aqueous layers was added solidNaBF4 (9.35 g, 85.2 mmol, 3 equiv), resulting in a bright-yellowprecipitate. The resulting suspension was extracted withdichloromethane (3 × 150 mL or until the washings become colorless).To the combined organic layers was added HBF4·Et2Ocomplex (3.46 mL, 28.4 mmol, 1 equiv). The solution wasswirled to achieve homogeneity then washed with water(1 × 100 mL) and aq. NaBF4 (1 M, 1 × 100 mL). The organic layerwas dried over solid NaBF4, filtered, and concentrated to dryness.The residue was purified by trituration with hexanes andfiltered. The solid was rinsed with n-pentane and dried in vacuoto give xanthylium 3 (10.6 g, 21.3 mmol, 75% yield) as a yelloworangesolid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 14920-81-1, its application will become more common.

Reference:
Article; White, Alexander R.; Wang, Leifeng; Nicewicz, David A.; Synlett; vol. 30; 7; (2019); p. 827 – 832;,
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. 61644-18-6, name is Chloromethyl isobutyrate, A new synthetic method of this compound is introduced below., Application In Synthesis of Chloromethyl isobutyrate

General procedure: To a solution of Compound 54B (150 mg, 0.24 mmol) in DMF (10 mL) was added chloromethyl isobutyrate (36 mg, 0.24 mmol) and Na2CO3 (50 mg, 0.48 mmol). The reaction mixture was stirred at 50 C for 3 hour. After cooling down to room temperature, the mixture was diluted with water (50 mL) and extracted with ethyl acetate (20 mL x 3). The combined extracts were washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to furnish Compound 54C. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used.

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; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 55666-43-8, name is tert-Butyl 3-bromopropanoate, 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 55666-43-8, Application In Synthesis of tert-Butyl 3-bromopropanoate

To a mixture of 2-sulfanyl-5,6,7,8-tetrahydro-4-quinazolinol (0.482 g, 2.64 mmol) and potassium carbonate (0.730 g, 5.29 mmol) in acetone was added tert-butyl 3-bromopropionate (0.663 g, 3.17 mmol). The mixture was stirred at 60C for 4 h (LC-MS indicated partial conversion to desired product). The solid was filtered off, and the solution was concentrated. The residual material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 0% to 50% EtOAc in hexane, to provide tert- butyl 3-((4-oxo-3,4,5,6,7,8-hexahydroquinazolin-2-yl)thio)propanoate (0.132 g, 0.425 mmol, 16.09 % yield) as white solid. lH NMR (400 MHz, DMSO-i/6) delta ppm 12.40 (br. s., 1 H) 3.24 (t, J=6.70 Hz, 2 H) 2.64 (t, J=6.75 Hz, 2 H) 2.42 – 2.49 (m, 2 H) 2.28 (br. s., 2 H) 1.60 – 1.78 (m, 4 H) 1.41 (s, 9 H). m/z (ESI) 31 1.2.

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:
Patent; AMGEN INC.; BREGMAN, Howard; BUCHANAN, John L.; CHAKKA, Nagasree; DIMAURO, Erin F.; GUNAYDIN, Hakan; GUZMAN PEREZ, Angel; HUA, Zihao; HUANG, Xin; WO2014/36022; (2014); 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. 18595-18-1, name is Methyl 3-amino-4-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H11NO2

Step 1. Preparation of methyl 1H-indazole-6-carboxylate (i-14b).Methyl 3-amino-4-methylbenzoate (i-14a) (5.0 g, 30.2 mmol) was dissolved in AcOH (140 mL). Sodium nitrite (2.1 g, 30.2 mmol) in water (3.5 mL) was added dropwise to the solution of starting material under ice-cooling at room temperature. The ice bath was removed and themixture was stirred overnight. Half of the solvent was evaporated, the mixture was diluted with water (80 mL) and extracted with EtOAc (3×30 mL). The collected organic phase was washed with water and brine (2×200 mL), dried and evaporated to afford the title compound (4.4 g), yield 83%. LCMS (ESI): calc?d for C9H8N202, [M+H]: 177, found: 177.

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 18595-18-1.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth Jay; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard Thomas; WO2014/28600; (2014); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 136333-97-6, name is Methyl 4-(2-bromoethyl)benzoate, molecular formula is C10H11BrO2, 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. category: esters-buliding-blocks

8e) 4-(2-Bromoethyl)benzyl alcohol To a suspension of LiAIH4 (4.5 mmol; 0.172 g) in anhydrous THF(5.0 ml) cooled to 00C was added dropwise a solution of methyl 4-(2- bromoethyl)benzenecarboxylate (1.0 g; 4.1 mmol) in anhydrous THF(10.0 ml). The reaction mixture was stirred for 5 minutes at room temperature and, after adding ice, was filtered through a Bchner filter.The solvent was removed under reduced pressure and the residue was extracted with ethyl acetate (3 * 100 ml). The combined organic phases were washed with saturated NaCI solution, dried over sodium sulfate and evaporated under reduced pressure. 800 mg (82.6%) of pure product were thus obtained as an oil .1H NMR (CDCI3, delta ppm): 3.22 (t, 2H); 3.62 (t, 2H); 4.72 (s, 2H); 7.25- 7.39 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 136333-97-6, its application will become more common.

Reference:
Patent; AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.p.A.; ALISI, Maria Alessandra; CAZZOLLA, Nicola; COSTI, Roberta; DI SANTO, Roberto; FURLOTTI, Guido; GUGLIELMOTTI, Angelo; POLENZANI, Lorenzo; WO2010/12611; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics