Month: August 2021

Synthetic Route of 431-47-0, 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. 431-47-0, name is Methyl 2,2,2-trifluoroacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Methyl trifluoroacetate (804 muL, 7.99 mmoles) and triethylamine (928 muL, 6.66 mmoles) were added to a suspension of glycine (500 mg, 6.66 mmoles) in methanol (2.5 mL). After the mixture was stirred vigorously for 18 h, 1 N HCl was added dropwise until the a pH of 2 was obtained. The reaction was added to ethyl acetate (30 mL) was washed with 1 N HCl (2 x 10 mL), dried over MgSO4, and concentrated in vacuo to yield the amide as a white solid (991 mg, 5.79 mmoles, 87%). LRMS: (CI+) calcd for C4H4NO3F3 (M + NH4): 189; found: 189. 1H NMR: spectrum is consistent with the predicted structure.

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 2,2,2-trifluoroacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Johns Hopkins University School of Medicine; EP1235851; (2006); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 88709-17-5, name is Ethyl 2-ethoxy-4-methylbenzoate, 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. COA of Formula: C12H16O3

Ethyl-2-ethoxy-4-methylbenzoate (3, 5 g, 24 mmol), freshly recrystallized N-bromosuccinimide (4.7 g, 26.4 mmol), ATBN (30 mg) were mixed in dry carbon tetrachloride (25 ml). Mixture was irradiated with light using 500 W lamp and was refluxed for 12 hr. Reaction mixture was cooled to room temperature and filtered to remove succinimide. Filtrate was washed with water fol lowed by brine wash, dried on anhydrous sodium sulfate and solvent was removed under vacuum. Residue solidifies on keeping. It was dissolved in petroleum.ether (10 ml) by refluxing. Solution was kept at room temperature for 6 hr. Product ethyl 4-bromomethyl-2-ethoxy-benzoate (4) crys tallized out as yellow crystals. Cooled in ice bath and filtered. Crystals were washed with ice-cold pet ether. Dried in air.

The synthetic route of Ethyl 2-ethoxy-4-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kalkote, Uttam R.; Gurjar, Mukund K.; Joshi, Shreerang V.; Kadam, Suresh M.; Naik, Sanjay J.; US2004/192955; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

89-91-8, name is Methyl 2,2-dimethoxyacetate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: Methyl 2,2-dimethoxyacetate

A mixture of 1-(2-bromophenyl)methanamine (4 g, 21.5 mmol) and methyl 2,2-dimethoxyacetate (3.60 g, 26.8 mmol) was stirred for 1 h at 80 C under nitrogen atmosphere. The mixture was cooled to room temperature and extracted with ethyl acetate (3*200 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with petroleum ether /ethyl acetate (1:1) to afford N-[(2-bromophenyl)methyl]-2,2-dimethoxyacetamide as a yellow solid (3 g, 48%). LCMS (ES, m/z): 288,290 [M+H]+.

The synthetic route of 89-91-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Forma Therapeutics, Inc.; Martin, Matthew W.; Zablocki, Mary-Margaret; Mente, Scot; Dinsmore, Christopher; Wang, Zhongguo; Zheng, Xiaozhang; (382 pag.)EP3636637; (2020); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 5616-81-9, A common heterocyclic compound, 5616-81-9, name is tert-Butyl 2-(methylamino)acetate, molecular formula is C7H15NO2, 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.

R2 H R = ISOBUTYL] R”= 9-fluorenylmethyl Sarcosine tert-butyl ester (500 mg, 3.7 mmol), triethylamine (0.3 ml) and N-Fmoc-leucine (1.4 g, 4 mmol) and PyBrop (1.75 g, 3.7 mmol) were added to dichloromethane (16 ml) in a 50 mL round bottomed flask with a magnetic stirring. The reaction mixture was left to stir at room temperature for 2.5 hours under an atmosphere of nitrogen. The solution was washed with dilute citric acid solution, sodium bicarbonate solution, brine, dried (MgSO4), filtered and concentrated under reduced pressure. The crude residue was purified by column chromatography on silica eluting with [30%] ethyl acetate-hexane to produce the dipeptide as a white solid (440 mg, [40%). 1H] NMR [(300MHZ,] CDC13) [57.] 67-7.19 (8H, m, ArH), 5.82-5. 79 (1H, m, NH), 4.70-4. 50 (3H, m, [NCH2] and a-CH), 4.07-3. 58 (3H, m, CHCH2), 3.06-2. 91 (3H, m, NCH3), 1.90-0. 84 [18H, m, [CH2CH (CH3)] 2 and tBu]. 13C NMR (75MHz, [CDC13)] [5173.] 77, 172.03, 156.09, 143.57, 143.37, 140.90, 127.33, 126.71, 124.85, 119.59, 66.72, 49.51, 48.96, 46.78, 41.29, 36.17, 24.20, 23.00, 21.27.

The synthetic route of 5616-81-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UBIQUITOUS TECHNOLOGIES PTY LTD; WO2004/7427; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 23680-40-2,Some common heterocyclic compound, 23680-40-2, name is Methyl 3-bromopropiolate, molecular formula is C4H3BrO2, 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: Methyl 3-bromopropiolate 2 (0.5 mmol), furan 1 (0.6 mmol) and distilled toluene (1.5 mL) were added in atwo-necked flask, and the mixture was stirred at reflux for 24 h under nitrogen atmosphere. After completion ofthe initial DielsAlder reaction, FeCl3 (10 mol%) was added under flow of nitrogen and the reaction mixture was stirred at reflux for 2 h. After removal of the solvent and filtration through a pad of silica, a product 4 was purified by silica gel column chromatography or PTLC using a mixture of ethyl acetate and n-hexane as an eluent.

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-bromopropiolate, its application will become more common.

Reference:
Article; Shinohara, Hiroyuki; Sonoda, Motohiro; Hayagane, Naoya; Kita, Shota; Tanimori, Shinji; Ogawa, Akiya; Tetrahedron Letters; vol. 55; 38; (2014); p. 5302 – 5305;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 1559-02-0, 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. 1559-02-0 name is Diethyl 1,1-cyclopropanedicarboxylate, 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.

To 500 ml of a three-necked flask was added 200 ml of methanol and 30 g of 1,1-cyclopropanedicarboxylic acid diethyl ester, cooled to 10 C, stir A solution of sodium hydroxide (NaOH 6.4 g, water 32 ml) was added dropwise, The reaction was carried out at room temperature for 3 hours, the reaction was terminated, the solvent was distilled off under reduced pressure, A white solid. To the solid was added 200 ml of water and 150 ml of ethyl acetate, ] Stir and layer, discard the organic phase. The aqueous layer was adjusted to pH 3 to 4 with 2 mol / L hydrochloric acid, Ethyl acetate extraction (200 ml x 2), The organic phase was dried over anhydrous sodium sulfate, filtered, The solvent was distilled off under reduced pressure, To give a colorless translucent oil

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diethyl 1,1-cyclopropanedicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Zhao Rui; Li Xinlu; Meng Qingyi; Zhang Xiquan; Shi Xiangfei; (25 pag.)CN103965104; (2017); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3399-21-1, name is cis-Dimethyl cyclohexane-1,4-dicarboxylate, 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 3399-21-1, Application In Synthesis of cis-Dimethyl cyclohexane-1,4-dicarboxylate

REFERENCE EXAMPLE 6 Monomethyl cis-1,4-cyclohexanedicarboxylate In 35 ml of methanol was dissolved 3.46 g of dimethyl cis-1,4-cyclohexanedicarboxylate, and 17.3 ml of 1N aqueous sodium hydroxide solution was added thereto, and the resulting mixture was stirred at room temperature for 1.5 hours. The solvent was distilled off under reduced pressure and the obtained aqueous solution was washed with ethyl acetate. The pH of the mixture was adjusted to 1 with diluted hydrochloric acid under ice-cooling and the mixture was extracted with ethyl acetate. The extracts were washed with an aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a colorless crystalline solid. Isopropyl ether was added to the crystalline solid and the crystalline solid was collected by filtration to obtain 1.76 g of the desired compound as a pale yellow crystalline solid. m.p.: 91-93 C.; NMR spectrum (CDCl3 +d6 -DMSO) delta ppm: 1.60-2.00(8H,m), 2.42-2.52(2H,m), 3.67(3H,s)

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; Sankyo Company, Limited; US5843973; (1998); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 20330-90-9, A common heterocyclic compound, 20330-90-9, name is Dimethyl 5-chloroisophthalate, molecular formula is C10H9ClO4, 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.

Step 1. Methyl 3-chloro-5-(hydroxymethyl)benzoate To a solution of dimethyl 5-chloroisophthalate (10.0 g, 43.7 mmol, Astatech) in methanol (50 mL) and methylene chloride (50 mL) at 0 C. was added sodium borohydride (5.5 g, 140 mmol, Aldrich). The reaction was allowed to gradually reach room temperature and stir for 1 hour. Additional portions of sodium borohydride (0.50 g, 13 mmol) were added at 2 hours and 3 hours. The reaction mixture was cooled to 0 C. and the reaction was quenched with water. The layers were separated and the aqueous layer was extracted with three portions of DCM. The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-25% EtOAc in hexanes. Yield: (4.51 g, 51%). 1H NMR (400 MHz, CDCl3) delta 7.92-7.90 (m, 1H), 7.90-7.88 (m, 1H), 7.57-7.55 (m, 1H), 4.73 (s, 2H), 3.92 (s, 3H); LCMS (M+H)+: 201.1203.1.

The synthetic route of 20330-90-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Rodgers, James D.; Shepard, Stacey; Wang, Haisheng; Shao, Lixin; US2015/175604; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 10203-58-4,Some common heterocyclic compound, 10203-58-4, name is Diethyl isobutylmalonate, molecular formula is C11H20O4, 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 solution of diethyl isobutylmalonate (50.0 g, 231 mmol) in anhydrous DMF (200 mL) cooled in an ice bath was added aH (60 %, 1 1.1 g, 277 mmol) in small portions. After the addition, the reaction mixture was stirred at 0C for 10 min and then at room temperature for 30 min. 5-Chloro-2-nirrobenzotrifluoride (47.3 g, 210 mmol) in anhydrous DMF (50 mL) was added dropwise and the mixture was stirred at room temperature for two days. The DMF was removed under high vacuum and the residue was diluted with ethyl acetate (400 mL). Water (400 mL) was added dropwise; ammonium chloride (25 g) was added and the layers were separated. The organic layer was washed with brine (400 mL), dried over sodium sulfate, and concentrated under reduced pressure to give a red-brown oil, which was purified by silica-gel flashchromatography eluting with heptane / ethyl acetate (12: 1) to give the desired product diethyl 2-isobutyl-2-(4-nilro-3-(trifiuoromethyl)phenyl)malonate (74.4 g, 87%) as a yellow oil:]H NMR (300 MHz, CDC13): delta 8.07 (s, 1 H), 7.94 (d, 2 H, J ——- 8.7 Hz), 7.88 (d, 2 I S . ./ 8.7 Hz), 4.25 (m, 4 H), 2.33 (d, 2 H, J= 6.6 Hz), 1.51 (m, 1 H), 1.26 (t, 6 H, J = 7.2 Hz), 0.84 (d, 6 H, J = 6.6 Hz);J 3C MR (75 MHz, CDC13): delta 169.23, 146.71 , 142.86, 132.94, 127.94 (q, J —— 5 Hz), 124.55, 123.12 (q, J —— 33 Hz), 121 .79 (q, J = 272Hz), 62.19, 65.59, 44.16, 24.66, 23.66, 13.89.

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

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; KOENIG, Gerhard; BLAIN, Jean-francois; WO2013/106328; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 50893-36-2,Some common heterocyclic compound, 50893-36-2, name is 1-Chloroethyl ethyl carbonate, molecular formula is C5H9ClO3, 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.

Preparation of 1-bromoethyl ethyl carbonate The reaction is carried out as in Example 5 starting with 1-chloroethyl ethyl carbonate in the presence of various catalysts and replacing the trimethylsilane bromide with acetyl bromide. The quantities of free agents employed and the results obtained are given in the table below.

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

Reference:
Patent; Societe Nationale des Poudres et Explosifs; US5202454; (1993); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics