Category: esters-buliding-blocks

These common heterocyclic compound, 73792-08-2, name is Methyl 4-amino-2-fluorobenzoate, 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. Formula: C8H8FNO2

General procedure: The obtained compound was dissolved in methylene chloride, and the solution was cooled to -10 C. Then, a methylene chloride solution (200 ml) of methyl 4-amino-2-fluorobenzoate (16.9 g, 100 mmol) and pyridine (10 ml) was added thereto, followed by stirring at room temperature for 2 hours. The reaction solution was washed with 0.1 N hydrochloric acid (200 ml×2). Then, the organic layers were combined and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=2:1 to 1:1) to obtain the title compound (12.4 g, 40%). [0715] MS (ESI) m/z 311 (M+H)+

The synthetic route of Methyl 4-amino-2-fluorobenzoate has been constantly updated, and we look forward to future research findings.

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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Some common heterocyclic compound, 454-31-9, name is Ethyl 2,2-difluoroacetate, molecular formula is C4H6F2O2, 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 Ethyl 2,2-difluoroacetate

Step 1: Preparation of 1-ethoxy-2,2-difluoroethanol To a solution of ethyl 2,2-difluoroacetate (200 g, 1.59 mol) in tert-butyl methyl ether (1200 mL) was added LiAlH4 (33 g, 0.78 mol) portionwise at 78 C. under a nitrogen atmosphere. Once the addition was complete, the reaction mixture was continually stirred for 6 hrs at 78 C. EtOH (75 mL, 98%) was added dropwise to quench the reaction at 78 C., and the resulting mixture was allowed to warm to rt. The mixture was poured into ice/water, and concentrated H2SO4 (100 mL) was added carefully with stirring. The mixture was extracted with tert-butyl methyl ether (two*1 L) and the combined organic layers were washed with water, dried over Na2SO4, and concentrated to afford crude material that was submitted to distillation under reduced pressure. The fraction was collected at 45-55 C./-0.1 MPa to afford the title compound (75 g, 37% yield) as a colorless liquid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 454-31-9, its application will become more common.

Reference:
Patent; PFIZER INC.; Cheng, Hengmiao; Johnson, JR., Theodore Otto; Kath, John Charles; Liu, Kevin Kun-Chin; Lunney, Elizabeth Ann; Nagata, Asako; Nair, Sajiv Krishnan; Planken, Simon Paul; Sutton, Scott Channing; US2013/79324; (2013); 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. 28170-07-2, name is Benzyl phenyl carbonate, A new synthetic method of this compound is introduced below., Safety of Benzyl phenyl carbonate

According to: Pittelkow, M.; Lewinsky, R.; and Christensen, J. B. Synthesis 2002, 15, 2195-2202.Benzyl phenylcarbonate (25,1 g, 1 10 mmol) was added dropwise to a solution of diethyl- enetriamine (5,16 g, 50 mmol) in dichloromethane (100 ml). The mixture was stirred for at least 20 h. The organic phase was washed with phosphate buffer (0.025 M K2HPO4, 0.025 MNaH2PO4, 2000 ml, pH adjusted to 3 with 2 M sulfuric acid). The organic phase was dried over sodium sulfate, filtered, and concentrated in vacuo.Yield: 25.2 g A portion (5 g) of the crude oil was mixed with hydrochloric acid (2 M, 15 ml). The mixture was stirred for 15 minutes. The mixture was filtered. The isolated solid was mixed with abs. ethanol (600 ml). The mixture was brought to reflux. The boiling mixture was decanted in order to remove insoluble impurities. The compound crystallized over night at 5 C.Yield: 2.84 g (white crystals) 1H-NMR (af-DMSO) delta: 8.96 (b, 2H), 7.51 (t, J = 5.56 Hz, 2H), 7.40-7.30 (b, 10H), 5,04 (s,4H), 3.33 (q, J = 6.06 Hz, 4H), 3.00 (b, 4H)13C- NMR (af-DMSO) delta: 156.6, 137.2, 128.7, 128.3, 128.2, 66.0, 46.8, 37.1LC-MS (ES-positive mode), m/z: 372.5 [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; NOVO NORDISK A/S; WO2006/79641; (2006); A2;,
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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. 711-01-3, name is Methyl adamantane-1-carboxylate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

Under a nitrogen atmosphere, 30.5 g (4.4 mol) of lithium metal (Li) was added to 2 L of tetrahydrofuran (THF) and stirred for 1 hour.Among these, 300 g (2.0 mol) of 2-adamantanone and 258.0 g (3.3 mol) of 2-chloropropane were added to THF 1000.The solution dissolved in mL,It dripped over 30 minutes, cooling so that 20 degrees C or less might be maintained.After completion of the addition, stir at 90 ° C. for 90 minutes,A THF solution of lithium 2-isopropyl-2-adamantyl alcoholate was obtained.362.0 g of methacrylic anhydride in this THF solution(2.4 mol) was dripped over 15 minutes, cooling so that 20 degrees C or less might be maintained. After completion of the dropwise addition, the mixture was stirred at 20 ° C. for 60 minutes to synthesize 2-isopropyl-2-adamantyl methacrylate.After completion of the reaction, 4 L of toluene was added, and further, 2000 mL of 0.2 N aqueous NaOH solution was added, and the mixture was stirred at 20 ° C. for 60 minutes.After removing the aqueous phase, washing was performed twice with 2 L of pure water.By distilling off the solvent from the organic phase,517.0 g (crude yield 99percent, GC purity 84.9percent) of crude 2-isopropyl-2-adamantyl methacrylate was obtained. continue,0.7 g of p-methoxyphenol as a polymerization inhibitor is added to the obtained crude 2-isopropyl-2-adamantyl methacrylate,0.1 kPa, 10 while bubbling dry air from the capillarySimple distillation at 0 to 120 ° C,369.0 g of distilled 2-isopropyl-2-adamantyl methacrylate (GC purity 88.2percent, referred to as ?distillate B?) was obtained.

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; Osaka Organic Chemical Industry Co., Ltd.; Kojima, Akio; Kono, Naoya; Uenoyama, Yoshitaka; (19 pag.)JP2019/34959; (2019); A;,
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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. 185629-32-7, name is Methyl 4-amino-3-fluorobenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 4-amino-3-fluorobenzoate

Example 38A Methyl 4-{[(6-bromo-3-methyl-2-phenylquinolin-4-yl)carbonyl]amino}-3-fluorobenzoate (0496) (0497) 1.00 g (2.55 mmol) of the compound from example 2A were dissolved in 10 ml of 49 DMF. To the solution were added 474 mg (2.80 mmol) of 158 methyl 4-amino-3-fluorobenzoate and 429 mg (3.82 mmol) of 153 potassium tert-butoxide. The reaction mixture was stirred at RT for 1 h and then stirred into a mixture of 50 ml of 44 ice-water, 50 ml of 159 ammonium chloride solution and 100 ml of 61 ethyl acetate. The organic phase was removed, washed twice with water and once with saturated sodium chloride solution, and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by means of column chromatography (silica gel, eluent: 5% ethyl acetate/95% cyclohexane?15% ethyl acetate/85% cyclohexane?45% ethyl acetate/55% 160 cyclohexane, Biotage). The product-containing fractions were concentrated and the residue was stirred in 10 ml of 45 tert-butyl methyl ether. The solids were filtered off, washed twice with 5 ml of tert-butyl methyl ether and then stirred in 4 ml of ethyl acetate for three days. The solids were then filtered off again and dried under reduced pressure. 810 mg (64% of theory, 99% purity) of the 161 title compound were obtained. (0498) 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=11.10 (s, 1H), 8.27 (t, 1H), 8.05 (d, 1H), 7.99 (d, 1H), 7.95-7.90 (m, 2H), 7.85 (dd, 1H), 7.64-7.62 (m, 2H), 7.58-7.51 (m, 3H), 3.89 (s, 3H), 2.43 (s, 3H). (0499) LC/MS (Method 1, ESIpos): Rt=1.27 min, m/z=493/495 [M+H]+.

The synthetic route of 185629-32-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharma Aktiengesekkschaft; BECK, Hartmut; THALER, Tobias; KAST, Raimund; MEIBOM, Daniel; MEININGHAUS, Mark; TERJUNG, Carsten; DELBECK, Martina; LUSTIG, Klemens; MUENSTER, Uwe; OLENIK, Britta; (100 pag.)US2017/260140; (2017); A1;,
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27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, 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. Safety of Methyl 4-amino-2-methoxybenzoate

(2) the above-mentioned the resulting 4-amino-2-methoxybenzoic acid methyl ester and N-chloro succinimide the mole ratio is that 1:1 in 70 C stirring in DMF solution of 3 hours later, is poured into the ice water is separated out in solid, filtering and drying to obtain 1.70 kg of 4-amino-5-chloro-2-methoxybenzoic acid methyl ester, in the yield of 88.3%.

The synthetic route of 27492-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing University of Science and Technology; Ma, Kefeng; Ren, Yu; Pan, Xiongfei; Wu, Jiating; Xu, Tongqiang; (6 pag.)CN105237422; (2016); A;,
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Application of 14062-18-1, 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 14062-18-1 as follows.

p-Methoxy toluene (1.83 g), ethanol (46 mg), di-tert-butyl peroxide (73 mg, 1 equivalent), and Pd(Xantphos)Cl2 (3.8 mg, 1 mol %) were added into a reaction kettle, into which 10 atm carbon monoxide was introduced. The reaction was heated to 120 C., and stirred at this constant temperature for 16 h. After the reaction was completed, carbon monoxide was discharged, and 82 mg ethyl p-methoxyphenylacetate was obtained by column chromatography, in a yield of 85%. 1HNMR (400 MHz, CDCl3) delta 1.23 (t, J=6.8 Hz, 3H), 3.54 (s, 2H), 3.79 (s, 3H), 4.11 (q, J=6.8 Hz, 2H), 6.84-6.88 (m, 2H), 7.18-7.22 (m, 2H); 13CNMR (100 MHz, CDCl3) delta 14.2, 40.5, 55.3, 60.8, 113.9, 126.3, 130.3, 158.7, 171.9; HRMS (ESI) calcd. for C11H14NaO3 [M+Na]: 217.0835. found: 217.0838. The ethyl p-methoxyphenylacetate obtained was dissolved in 1,4-dioxane. 6 N sodium hydroxide solution was added, and the reaction was heated to 60 C. After 2 h of reaction, the pH value was adjusted to 1 by adding 2 N hydrochloric acid. After removing the organic solvent under reduced pressure, 64 mg product p-methoxyphenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 91%.

According to the analysis of related databases, 14062-18-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences; Huang, Hanmin; Xia, Chungu; Xie, Pan; US2013/303798; (2013); A1;,
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Related Products of 66315-16-0,Some common heterocyclic compound, 66315-16-0, name is Methyl 3-amino-4-(methylamino)benzoate, molecular formula is C9H12N2O2, 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.

800 mg (4.4 mmol) s3 was dissolved in 10 mLacetic acid, 336 mg (4.8 mmol) sodium nitrite was added slowly.The mixture was stirred for 18 h at room temperature, then poured into 30 mL water, neutralized with saturated solution of sodium bicarbonate, extracted with 50 mL ethyl acetate, washed with 20 mL water, dried with anhydrous sodium sulfate overnight. The filtrate was concentrated by vacuum distillation to obtain brown solid, recrystallized from ethyl acetate and hexane to afford pale brown solid of s4 300 mg, yield 35%.1H NMR(400 MHz, CDCl3): d8.78 (s, 1H, ArH), 8.19 (d, 1H, J = 8.8 Hz, ArH), 7.55 (d, 1H, J = 8.8 Hz, ArH), 4.33 (s, 3H, OCH3), 3.98 (s, 3H, NCH 3 );13C NMR (100 MHz,CDCl3): d 166.6, 145.6, 135.6, 128.2, 126.3, 122.9, 109.0, 52.4, 34.4.HRMS (EI) calcd. for C9H9N3O2 [M]+: 191.0695, found 191.0697.

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-amino-4-(methylamino)benzoate, its application will become more common.

Reference:
Article; Chang, Kang; Chen, Jian-Qin; Shi, Yan-Xia; Sun, Mei-Jian; Li, Peng-Fei; Zhao, Zhen-Jiang; Zhu, Wei-Ping; Li, Hong-Lin; Xu, Yu-Fang; Li, Bao-Ju; Qian, Xu-Hong; Chinese Chemical Letters; vol. 28; 4; (2017); p. 919 – 926;,
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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. 51760-21-5, name is Dimethyl 5-bromoisophthalate, A new synthetic method of this compound is introduced below., Computed Properties of C10H9BrO4

Dimethyl-5-bromoisophthalate (3 g, 11.0 mmol) was dissolved in acetone-H2O (2:1 v/v, 60 mL) and NaOH (0.40 g, 11.0 mmol) was added. The reaction mixture was allowed to stir for 4 h. Acetone was removed under reduced pressure and the aqueous layer was washed with EtOAc, acidified to pH ? 2-3 using 1.5N HCl, and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to yield 3-bromo-5-(methoxycarbonyl)benzoic acid (2.55 g, yield 89%): 1H NMR (300 MHz, DMSO-d6) delta 13.75 (br s, 1 H), 8.40 (d, J = 1.0 Hz, 1 H), 8.26 (d, J = 1.4 Hz, 1 H), 8.23 (d, J = 1.0 Hz, 1 H), 3.89 (s, 3H). MS (ESI) m/z: Calculated for C9H7BrO4: 257.95; found: 258.0 (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; Tempero Pharmaceuticals, Inc.; BALOGLU, Erkan; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby; EP2533783; (2015); B1;,
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Synthetic Route of 680-65-9, A common heterocyclic compound, 680-65-9, name is Diethyl difluoromalonate, molecular formula is C7H10F2O4, 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: 2,2-difluoropropane-1,3-diol To a solution of diethyl difluoromalonate (3.77 g, 19.22 mmol) in THF (19.22 ml) at 0 C., was added Lithium Aluminium Hydride (1M in THF, 30.8 ml, 30.8 mmol) drop-wise. The reaction mixture was brought to ambient temperature and then stirred for 16 hours. The reaction mixture was then slowly poured onto an ice-cold suspension of 4 g of Na2SO4.10H2O in 20 mL of THF. This was stirred for 1 h and the resulting slurry was filtered, rinsed with 1:3 MeOH/EtOAc. The filtrate was collected and concentrated to give the title compound (1.7 g, 15.17 mmol, 79% yield) as a white paste.

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; LEWIS, Richard T.; ALLEN, Jennifer R.; CHENG, Yuan; CHOQUETTE, Deborah; EPSTEIN, Oleg; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; HUA, Zihao; HUNGATE, Randall W.; HUMAN, Jason Brooks; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; MINATTI, Ana Elena; OLIVIERI, Philip; ROMERO, Karina; RUMFELT, Shannon; RZASA, Robert M.; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; XUE, Qiufen; ZHENG, Xiao; ZHONG, Wenge; US2014/107109; (2014); A1;,
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