Category: esters-buliding-blocks

Application of 681465-85-0, 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. 681465-85-0, name is Methyl 4-amino-3-isopropoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The aryl carboxylic acid monomer (6 mmol, comp. 4-6), Mukaiyama reagent (6 mmol) and Et3N (12 mmol) were dissolved in an anhydrous dichloromethane (100 mL). The solution was refluxed for 15 min. under N2. Then a solution of the corresponding arylamine (5 mmol, comp. 7-9) in an anhydrous dichloromethane (20 mL) was added to the reaction mixture and resulting solution was refluxed for 2 days. The solvent was evaporated under vacuum and the residue was subjected to the column of silica gel using the mixture of hexanes/ dichloromethane (2:3) as an eluent to give amide coupling products in moderate to good yields. Note: for the synthesis of 18, 2.5 eq. of corresponding aryl amine over 2-methoxyisophthalic acid was used.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-amino-3-isopropoxybenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Kulikov, Oleg V.; Incarvito, Christopher; Hamilton, Andrew D.; Tetrahedron Letters; vol. 52; 29; (2011); p. 3705 – 3709;,
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Electric Literature of 3044-06-2,Some common heterocyclic compound, 3044-06-2, name is Diethyl 2-(1-ethoxyethylidene)malonate, molecular formula is C11H18O5, 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: Diethyl ethoxymethylenemalonate (4.6mmol) were add to a solution of sodium hydride (9.7mmol) and compound 14a-l (4.2mmol) in ethanol (20mL), the reaction mixture was stirred at 80C for 2h. After the reaction completed, the mixture was added 10mL 6M hydrochloric acid and stirred for 0.5h, then the precipitate was collected by filtration. The resulting residue was recrystallized from ethanol to yield ethyl 2-(4-alkoxyphenyl-3-cyano)-6-oxo-1,6-dihydropyrimidine-5-carboxylate(15a-l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Diethyl 2-(1-ethoxyethylidene)malonate, its application will become more common.

Reference:
Article; Mao, Qing; Dai; Xu, Gaoyang; Su, Yu; Zhang, Bing; Liu, Dan; Wang, Shaojie; European Journal of Medicinal Chemistry; vol. 181; (2019);,
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Adding a certain compound to certain chemical reactions, such as: 89-91-8, name is Methyl 2,2-dimethoxyacetate, 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 89-91-8, name: Methyl 2,2-dimethoxyacetate

Compound 7 (15mmol) and methyl 2,2-dimethoxypropionate (30mmol) were kept in a 10mL screw-capped vial was stirred at 80C overnight. The reaction mixture was loaded on silica and resulting 110 dimethoxy acetamide intermediate 8 was purified by silica column chromatography using hexane and ethylacetate at a ratio of 2:1. The resulted compound without further purification was dissolved in 5mL concentrated sulfuric acid and stirred at 40C overnight. Subsequently, the acidic solution poured into ice-water, and the precipitate was collected and washed with water and diluted sodium bicarbonate solution [16]. The yield was 42%.1H NMR (500MHz, DMSO-d6) delta 8.91 (s, 1H, H1-isoquinoline), 7.64 (d, J=8.4Hz, 1H), 7.49 (d, J=8.4Hz, 1H), 6.87 (s, 1H, H4-isoquinoline), 5.74 (bs, 1H, OH), 2.54 (s, 3H, CH3).

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:
Article; Assadieskandar, Amir; Yu, Caiqun; Maisonneuve, Pierre; Liu, Xu; Chen, Ying-Chu; Prakash, G.K. Surya; Kurinov, Igor; Sicheri, Frank; Zhang, Chao; European Journal of Medicinal Chemistry; vol. 146; (2018); p. 519 – 528;,
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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. 15963-46-9, name is Methyl 3-chlorocyclobutanecarboxylate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 3-chlorocyclobutanecarboxylate

Step 1: To a 3-neck flask that had been purged and maintained with an inert atmosphere of nitrogen, was placed a solution of phenol (111 g, 1.18 mol) in DMSO (2000 mL). To thissolution was added potassium tert-butoxide (240 g, 2.14 mol), and the mixture was heated to80C with vigorous stirring under an argon atmosphere for 15 minutes. To the above solution was added methyl 3-chlorocyclobutanecarboxylate (160 g, 1.08 mol) dropwise with stirring followed by tetrabutylammonium iodide (238 g, 0.646 mol). The reaction mixture was stirred for 1.5 h at 80C. The mixture was cooled to 10C, quenched with water (30 mL), and theaqueous layer was extracted with EtOAc (3 x 1000 mL). The combined organic layers were washed with brine (200 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (1:40 EtOAc:petroleum ether) to afford methyl 3-phenoxycyclobutanecarboxylate as a solid.

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; MERCK SHARP & DOHME CORP.; FISCHER, Christian; BOGEN, Stephane, L.; CHILDERS, Matthew, L.; LLINAS, Francesc Xavier Fradera; ELLIS, J. Michael; ESPOSITE, Sara; HONG, Qingmei; HUANG, Chunhui; KIM, Alexander, J.; LAMPE, John, W.; MACHACEK, Michelle, R.; MCMASTERS, Daniel, R.; OTTE, Ryan, D.; PARKER, Dann, L., Jr.; REUTERSHAN, Michael; SCIAMMETTA, Nunzio; SHAO, Pengcheng, P.; SLOMAN, David, L.; UJJAINWALLA, Feroze; WHITE, Catherine; WU, Zhicai; YU, Yang; ZHAO, Kake; GIBEAU, Craig; BIFTU, Tesfaye; BIJU, Purakkattle; CHEN, Lei; CLOSE, Joshua; FULLER, Peter, H.; HUANG, Xianhai; PARK, Min, K.; SIMOV, Vladimir; WITTER, David, J.; ZHANG, Hongjun; (297 pag.)WO2016/89797; (2016); A1;,
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Reference of 314298-22-1, The chemical industry reduces the impact on the environment during synthesis 314298-22-1, name is Methyl 5-bromo-4-fluoro-2-methoxybenzoate, I believe this compound will play a more active role in future production and life.

Step 3: Cool in ice a solution of the product of Step 2 (1.15 g, 4.1 mmol) in THF (15 ml). Add dropwise BH3.Me2S (2.0M in THF, 4.2 ml, 8.4 mmol). Heat at 60 C. 18 h, allow to cool, quench with methanol, concentrate and partition with EtOAc and sat. NaHCO3. Wash with water, then brine, dry (MgSO4) and concentrate to obtain the alcohol as a yellow oil.

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 5-bromo-4-fluoro-2-methoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Schering Corporation; US2004/220194; (2004); A1;,
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Related Products of 23680-40-2, The chemical industry reduces the impact on the environment during synthesis 23680-40-2, name is Methyl 3-bromopropiolate, I believe this compound will play a more active role in future production and life.

General procedure: Methyl 3-bromopropiolate 2 (0.5 mmol), furan 1 (0.6 mmol) and distilled toluene (1.5 mL) were added to atwo-necked flask, and the mixture was stirred at reflux for 24 h under nitrogen atmosphere. After completion ofthe initial DielsAlder reaction, silica gel (150 mg) was added under flow of nitrogen and the mixture wasstirred at reflux for 2 h. After removal of the solvent and filtration, a product 4 was purified by silica gelcolumn chromatography or PTLC using a mixture of ethyl acetate and n-hexane as an eluent.

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 3-bromopropiolate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Shinohara, Hiroyuki; Sonoda, Motohiro; Hayagane, Naoya; Kita, Shota; Tanimori, Shinji; Ogawa, Akiya; Tetrahedron Letters; vol. 55; 38; (2014); p. 5302 – 5305;,
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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. 955887-09-9, name is tert-Butyl 4-bromo-2,6-difluorobenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: tert-Butyl 4-bromo-2,6-difluorobenzoate

To tert-butyl 4-bromo-2,6-difluorobenzoate (1.47 g, 5.00 mmol), DMA (10 ml), copper(I) chloride (990 mg, 10.0 mmol), triethylamine (1.74 ml, 12.5 mmol), and TMSN3 (1.32 ml, 10.0 mmol) were added, followed by stirring at 100 C. for 16 hours. To the reaction liquid, water was added, followed by extraction with ethyl acetate (10 ml¡Á3). After concentration under reduced pressure, the residue was purified by reversed-phase HPLC (H2O containing 0.1% TFA/CH3CN system), followed by freeze-drying, to obtain a TFA salt (810 mg, 71%) of the title compound. [1075] MS (ESI) m/z 230 (M+H)+

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; AJINOMOTO CO., LTD.; Ueno, Hirokazu; Yamamoto, Takashi; Takashita, Ryuta; Yokoyama, Ryohei; Sugiura, Toshihiko; Kageyama, Shunsuke; Ando, Ayatoshi; Eda, Hiroyuki; Eviryanti, Agung; Miyazawa, Tomoko; Kirihara, Aya; Tanabe, Itsuya; Nakamura, Tarou; Noguchi, Misato; Shuto, Manami; Sugiki, Masayuki; Dohi, Mizuki; US2015/51395; (2015); A1;,
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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. 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 3-bromo-4-fluorobenzoate

Cesium carbonate (3.1 g, 9.6 mmol) was added to 4-fluoro-2,6-dimethylphenol (0.9 g, 6.4 mmol) and methyl 3-bromo-4-fluorobenzoate (1.57 g, 6.7 mmol) ) in a solution of dimethyl sulfoxide (10 mL). The reaction mixture was stirred at 80 C for 12 hr, then cooled to room temperature, then water (50mL), ethyl acetate (50mL*2). The organic phase was washed with brine (25 mL*4) and evaporated to dryness. The crude product was separated by column ( petroleum ether: ethyl acetate = 20:1) to give methyl 3-bromo-4-(4-fluoro-2,6-dimethylphenoxy) benzoate (1.4 g, 3.97 mmol , molar yield 62%).

The synthetic route of 82702-31-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Hansen Bio-pharmaceutical Technology Co., Ltd.; Jiangsu Haosen Pharmaceutical Group Co., Ltd.; Sun Changan; Zhang Xiaoyu; Chen Gangsheng; Zong Shumin; (45 pag.)CN109836385; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, 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 252881-74-6, Product Details of 252881-74-6

Example 32Step 1: ( 15R,19R)-tert-butyl 15-(((( 9H-fluoren-9-yl)methoxy)carbonyl)amino)-19-( dodecyloxy)-14- oxo-4, 7, 10,21 -tetraoxa-17-thia-13-azatritriacontan-l-oate[000538] To a solution of (?)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(((?)-2,3- bis(dodecyloxy)propyl)thio)propanoic acid (1 eq, from example 20, step 5) and HBTU (1.2 eq) inDCM (0.06 M) was added DIEA (3.5 eq), followed by teri-butyl 3-(2-(2-(2- aminoethoxy)ethoxy)ethoxy)propanoate (1.2 eq). The reaction was stirred at room temperature for2 hours. The crude mixture was purified by flash chromatography on a COMBIFLASH system(ISCO) using 0-5% MeOH/DCM to give the title product as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, and friends who are interested can also refer to it.

Reference:
Patent; IRM LLC; WU, Tom Yao-Hsiang; ZOU, Yefen; HOFFMAN, Timothy Z.; PAN, Jianfeng; WO2011/119759; (2011); A1;,
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Related Products of 56441-97-5,Some common heterocyclic compound, 56441-97-5, name is Methyl 4-(benzyloxy)-3-methoxybenzoate, molecular formula is C16H16O4, 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.

4.1.4 Methyl 4-benzyloxy-5-methoxy-2-nitrobenzoate (12) To a suspension of intermediate 11 (10.1 g, 37 mmol) in AcOH (100 mL) was slowly added 70% HNO3 (20 mL). Subsequently, the mixture was heated to 50 C for 5 h, then cooled to room temperature and poured into ice water (500 mL). After stirring for 1 h, the resulting precipitate was filtered off, washed with water and dried to obtain the nitro compound 12 as a white solid. Yield: 86%, mp: 126-128 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-(benzyloxy)-3-methoxybenzoate, its application will become more common.

Reference:
Article; Cheng, Weiyan; Yuan, Youting; Qiu, Ni; Peng, Peng; Sheng, Rong; Hu, Yongzhou; Bioorganic and Medicinal Chemistry; vol. 22; 24; (2014); p. 6796 – 6805;,
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