Category: esters-buliding-blocks

35179-98-7, name is Chloromethyl ethyl carbonate, 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. SDS of cas: 35179-98-7

To a solution of (2R,4R)-4-(t-butoxyoxalylamino)-5-(3?-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid (100 mg, 220 mumol) and chloromethyl ethyl carbonate (61 mg, 440 mol) in DMF (3 mL) was added 2,6-lutidine (72 mg, 660 mumol) and NaI (33 mg, 220 mumol). After stirring at room temperature for 24 hours, the mixture was diluted with water (20 mL) and extracted with EtOAc (2¡Á20 mL). The combined organic layers were washed with saturated aqueous NaCl (2¡Á70 mL), dried over anhydrous Na2SO4, filtered, and concentrated to give the crude product which was further purified by preparative TLC (PE:EtOAc=2:1) to yield Compound 1 (40 mg) as a yellow solid. LC-MS: 572[M+Na]+.

The synthetic route of 35179-98-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HUGHES, Adam D.; FENSTER, Erik; FLEURY, Melissa; GENDRON, Roland; US2013/109639; (2013); A1;,
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Some common heterocyclic compound, 15568-85-1, name is 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione, molecular formula is C8H10O5, 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. Quality Control of 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

A mixture of sulfone 5 (1.58g, 7.5mmol) and 15(558 mg, 3 mmol) in freshly distilled DMF (9 mL) was added to a mixture of HgCl2 (49mg, 0.18 mmol)and Mg (183mg, 7.5 mmol) in DMF (3 mL) at ambient temperature. The reaction was heated to 75 Cand stirred for an additional 3 h. The reaction was cooled to rt and quenched with 7M HCl. The reactionmixture was then heated to 110 C and stirred for an hour. The reaction mixture was cooled to rt andextracted with diethyl ether (3), dried over MgSO4 and concentrated under reduced pressure and dried toobtain crude carboxylic acid. The crude acid was dissolved in dry DMF and added to a round-bottomedflask containing anhydrous K2CO3 (830 mg, 6 mmol) after which benzyl bromide (0.7 mL, 6 mmol) wasadded. The mixture was stirred for 2 h and then diluted with water and extracted with diethyl ether (3),washed with brine and dried over MgSO4. The ethereal layer was concentrated under reduced pressure toobtain the crude ester

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15568-85-1, its application will become more common.

Reference:
Article; Sakavuyi, Kaumba; Petersen, Kimberly S.; Tetrahedron Letters; vol. 54; 45; (2013); p. 6129 – 6132;,
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Synthetic Route of 73368-41-9, 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. 73368-41-9, name is Ethyl 4-amino-3-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(R)-ethyl 4-((8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2- yl)amino)-3-methoxybenzoate (i?)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (88.4 mg, 0.30 mmol, 1 eq), ethyl 4-amino-3-methoxybenzoate (70.3 mg, 0.36 mmol, 1.2 eq), Pd2dba3 (13.7 mg, 0.015 mmol, 5 mol%), XPhos (21.5 mg, 0.045 mmol, 15 mol%) and K2C03 (166 mg, 1.2 mmol, 4 eq) were dissolved in tBuOH (3 mL, 0.1 M) and heated to 100 C for 20 hours. The mixture was filtered through celite, washed with DCM and condensed. Purification by column chromatography (ISCO, 4 g silica column, 0-100% EtOAc/hexanes, 12 minute gradient) gave the desired product as a dark yellow oil (119 mg, 0.262 mmol, 87%). 1H NMR (400 MHz, Chloroform-;/) delta 8.57 (d, J= 8.5 Hz, 1H), 7.68 (tt, J = 4.2, 2.1 Hz, 3H), 7.53 (d, J= 1.4 Hz, 1H), 4.50 (q, J= 7.4 Hz, 1H), 4.36 (qd, J= 7.1, 1.2 Hz, 2H), 4.22 (dd, J= 7.8, 3.6 Hz, 1H), 3.96 (d, J= 1.2 Hz, 3H), 3.32 (d, J= 1.3 Hz, 3H), 2.22 – 2.10 (m, 1H), 2.04 – 1.96 (m, 1H), 1.89 – 1.78 (m, 4H), 1.70 (dq, J= 14.2, 8.2, 7.4 Hz, 4H), 1.39 (td, J= 7.1, 1.2 Hz, 3H), 0.91 – 0.82 (m, 3H). LCMS 453.80 (M+H).

The synthetic route of Ethyl 4-amino-3-methoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BRADNER, James, E.; GRAY, Nathanael; QI, Jun; MCKEOWN, Michael, R.; BUCKLEY, Dennis; WO2015/117055; (2015); A1;,
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Electric Literature of 454-31-9, These common heterocyclic compound, 454-31-9, name is Ethyl 2,2-difluoroacetate, 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 2: Preparation of 4,4-difluoro-1-(3-fluoro-4-methoxyphenyl)-butane-1,3-dione Ethyl difluoroacetate (4.06 g, 32.7 mmol) was dissolved in methyl tert-butyl ether (50 mL). To the stirred solution was added 25 weight % sodium methoxide (7.07 g, 32.7 mmol) followed by 3′-fluoro-4′-methoxyacetophenone from Step 1 (5.0 g, 29.7 mmol). After stirring for 16 hours, 1N HCl (50 mL) was added. The organic layer was collected and washed with water (2*50 mL), dried over anhydrous MgSO4, filtered, and added to hexanes to precipitate a tan solid (7.0 g, 96%): mp 70-72 C.

The synthetic route of 454-31-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; G.D. Searle & Co.; US6407140; (2002); B1;,
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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. 29263-94-3, name is Diethyl 2-bromo-2-methylmalonate, A new synthetic method of this compound is introduced below., Product Details of 29263-94-3

A mixture of diethyl 2-bromo-2-methylmalonate (1 equiv.), malononitrile (1 equiv.) and potassium t-butoxide (1 equiv.) in THF was heated to reflux for 15 h. The mixture was diluted with ethyl acetate and saturated aqueous ammonium chloride solution and the phases were separated. The aqueous phase was extracted twice with ethyl acetate. The combined organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to give an oil. The oil was purified by silica gel chromatography (10-15%) ethyl acetate in hexane gradient) to give diethyl 2-(dicyanomethyl)-2-methylmalonate (5.76 g, 32 %> yield) as a colorless oil. 1H NMR (500 MHz, CDC13) delta ppm 4.53 (s, 1 H), 4.27 – 4.39 (m, 4 H), 1.81 (s, 3 H), 1.33 (t, 6 H).

The synthetic route of 29263-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRONWOOD PHARMACEUTICALS, INC.; BARDEN, Timothy Claude; SHEPPECK, James Edward; RENNIE, Glen Robert; RENHOWE, Paul Allan; PERL, Nicholas; NAKAI, Takashi; MERMERIAN, Ara; LEE, Thomas Wai-Ho; JUNG, Joon; JIA, James; IYER, Karthik; IYENGAR, Rajesh R.; IM, G-Yoon Jamie; (293 pag.)WO2016/44447; (2016); A1;,
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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. 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Ethyl 2-(4-bromophenyl)acetate

Example 13A Ethyl 2-(4-bromophenyl)-2-methylpropanoate 2.0 g (8.2 mmol) of ethyl (4-bromophenyl)acetate were dissolved in 50 ml of DMF, and 0.7 g (18 mmol) of sodium hydride in mineral oil (60%) were added at RT. The mixture was stirred at RT for 30 minutes, after which 2.9 g (20.6 mmol) of iodomethane were added. The mixture was then stirred at RT overnight. The mixture was diluted with ethyl acetate and extracted first with water and then with saturated sodium chloride solution. The organic phase was separated off, dried over magnesium sulphate and filtered, and the filtrate was concentrated. The residue was purified by preparative HPLC [Reprosil C18, 10 mum, 250 mm*40 mm (30% methanol/70% water to 100% methanol) over a run time of 25 min]. After HPLC control, the product-containing fractions were combined and concentrated. This gave 1.75 g (78% of theory) of an oil. GC-MS [Method 5]: Rt=5.10 min; MS(ESIpos): m/z=270/272 (M+) 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=1.11 (t, 3H), 1.48 (s, 6H), 4.06 (q, 2H), 7.24-7.29 (m, 2H), 7.50-7.54 (m, 2H)

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 14062-25-0.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; BECKER-PELSTER, Eva Maria; BUCHGRABER, Philipp; BUCHMUeLLER, Anja; ENGEL, Karen; GNOTH, Mark Jean; HIMMEL, Herbert; KAST, Raimund; KELDENICH, Joerg; KLAR, Juergen; KNORR, Andreas; LANG, Dieter; LINDNER, Niels; SCHMECK, Carsten; SCHOHE-LOOP, Rudolf; TINEL, Hanna; TRUeBEL, Hubert; WUNDER, Frank; (97 pag.)US2016/318866; (2016); 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 91-44-1 as follows. Formula: C14H17NO2

To a 25 mL reaction tube, add Na2CO3 (63.6 mg, 0.60 mmol), 69.4 mg (0.30 mmol, 1 equivalent) of compound C-2,After replacing with argon three times, 1 mL of acetone (Acetone) + 1 mL of N, N-methylformamide (DMF) was added.After injecting 155 muL (0.90 mmol) of compound E-2 and stirring for 24 hours under blue light irradiation, compound H-4 was obtained with a yield of 82%.

According to the analysis of related databases, 91-44-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zunyi Medical University; He Chunyang; Mao Ting; Zhao Liang; Li Xiaofei; (13 pag.)CN110642831; (2020); A;,
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Synthetic Route of 21597-54-6, 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. 21597-54-6, name is Methyl 3-amino-2-naphthoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Synthesis of Intermediate (C) (0258) 15 g (74.5 mmol) of Intermediate (B) was added to 200 mL of tetrahydrofuran (THF). Then, while slowly stirring the resulting mixture, 5.72 g (149 mmol) of NaH (60% dispersion in mineral oil) was added dropwise thereto. The obtained reaction mixture was refluxed at a temperature of about 60 C. for about 72 hours, cooled to room temperature, and 250 mL of distilled water was added thereto to complete the reaction. 500 mL of 2N HCl was slowly added to the resulting reaction mixture, followed by stirred for about 60 minutes. The formed solid product was subjected to filtration and washed using distilled water. The formed solid product was vacuum-dried, thereby obtaining 8.07 g of Intermediate (C) (yield: 64%). 1H NMR (300 MHz, DMSO-d6): 10.5 (s, 2H), 7.92 (m, 4H), 7.88 (m, 4H), 7.64 (s, 2H), 7.46 (s, 2H).

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

Reference:
Patent; SAMSUNG DISPLAY CO., LTD.; INDUSTRY-ACADEMIC COOPERATION FOUNDATION GYEONGSANG NATIONAL UNIVERSITY; Kim, Mikyung; Kim, Yunhi; Kwon, Soonki; Kim, Heeyeon; Park, Yunjee; Jeong, Hyein; Hwang, Jaeyoung; (77 pag.)US2017/77422; (2017); A1;,
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Some common heterocyclic compound, 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, molecular formula is C8H6BrFO2, 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. Quality Control of Methyl 4-bromo-3-fluorobenzoate

To a solution of 8 (1.5g, 7.69mmol) in 1,4-dioxane was added 2eq. l-methyl-3- trifluoromethylpyrazole-5-boronic acid, Pd(dppf)2C12 (0.5g) and 3eq.K3P04. 3H20. The reaction mixture was sparged with nitrogen for 10 minutes. And the resulting mixture was stirred at 85C for 15 hours under the N2. EA/brine work and followed by prep HPLC purification to give 1.3 g compound 9. l .lg of 10 was obtained after hydrolysis with aq. LiOH.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 849758-12-9, its application will become more common.

Reference:
Patent; CALCIMEDICA, INC.; WHITTEN, Jeffrey P.; PEI, Yazhong; CAO, Jianguo; WANG, Zhijun; ROGERS, Evan; DYCK, Brian; GREY, Jonathan; WO2011/139765; (2011); A2;,
Ester – Wikipedia,
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Application of 927-68-4, These common heterocyclic compound, 927-68-4, name is 2-Bromoethyl 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.

A solution of Intermediate 11 (470 mg, 1.50 mmol), 2-bromoethyl acetate (1.00 g, 5.99 mmol) and DBU (913 mg, 6.01 mmol) in DMF (3 ml) was heated under argon at 80QC for 1.5 h. On cooling the reaction mixture was diluted with EtOAc (50 ml) and 1M aqueous HCI (50 ml). The organic layer was separated, washed with water (40 ml) and brine (40 ml), dried (Na2SO4) and evaporated. The crude product was chromatographed on an Isolute Si Il cartridge (20 g) eluting with 50-100% EtOAc in pentane.Yield: 457 mg (63%)LC-MS (Method 1): Rt 3.22 min, m/z 486 [MH+]

Statistics shows that 2-Bromoethyl acetate is playing an increasingly important role. we look forward to future research findings about 927-68-4.

Reference:
Patent; ARGENTA DISCOVERY LIMITED; WO2007/107706; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics