Category: esters-buliding-blocks

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

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 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

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 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

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

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

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

Application of 6627-89-0, These common heterocyclic compound, 6627-89-0, name is tert-Butyl phenyl carbonate, 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 36A; To a solution of 8.00 g (76.7 mmol) pentane-1 ,3-diamine in 150 ml anhydrous ethanol 29.0 ml (153 mmol) te/t-butyl-phenyl-carbonate are added. The mixture is heated to reflux for 4 h. After cooling to room temperature 500 ml water is added, the mixture is adjusted to pH 3 with 2M HCI and extracted two times with 500 ml DCM. The aqueous layer is separated, adjusted to pH 12 with 2M sodium hydroxide solution and extracted three times with 500 ml DCM. The organic phases are combined, dried and evaporated under reduced pressure to yield the product as an oil. The product is used for the next reaction without further purification, yield: 15.5 g (100%) LC-MS (Method 1s): RT = 0.91 min MS (ESI pos): m/z = 203 (M+H)+

The synthetic route of 6627-89-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/92566; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, 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. name: Methyl trans-4-aminocyclohexanecarboxylate hydrochloride

To a stirred solution of 6-((1,6-naphthyridin-2-yl)amino)-4-(cyclopropylamino)nicotinic acid (1.85 g, 5.76 mmol, Intermediate N) and methyl (1R,4R)-4-aminocyclohexane-1-carboxylate hydrochloride (1.34 g, 6.91 mmol) in DMF (10 mL) was added DIPEA (5 mL, 28.8 mmol) and PyBOP (4.5 g, 8.64 mmol) at rt. The resulting reaction mixture was stirred at rt for 16 h. The reaction mixture was then transferred into ice water and the resulting precipitate was filtered off, and dried reduced pressure. The crude product was purified using silica gel column chromatography (7% MeOH-DCM) to give methyl (1r,4r)-4-(6-((1,6-naphthyridin-2-yl)amino)-4-(cyclopropylamino)nicotinamido)cyclohexane-1-carboxylate as light a green solid (1.3 g, 49%). LC-MS (ESI+) m/z 460.54 (M+H)+

The synthetic route of Methyl trans-4-aminocyclohexanecarboxylate hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics