Month: August 2021

These common heterocyclic compound, 135908-33-7, name is Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, 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. Safety of Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate

General method D, 4-(isopropoxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylate.

The synthetic route of Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cyteir Therapeutics, Inc.; Castro, Alfredo C.; McComas, Casey Cameron; Vacca, Joseph; Maclay, Tyler; (132 pag.)US2019/77799; (2019); 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. 35065-86-2, name is 3-Bromophenyl acetate, A new synthetic method of this compound is introduced below., Formula: C8H7BrO2

3-Bromophenol (5) (10.0 g, 58 mmol) was dissolved in pyridine(30 mL) under ice-bath and was stirred for 30 min. Acetic anhydride (8.3 mL, 88 mmol) was added dropwise into above mixture at the same temperature. The ice-bath was removed after dropping and the mixture was stirred for 2 h. Concentrated HCl and ice-water (300 mL) was added to neutralize pH to 7. The mixture was extracted with AcOEt (100 mL 3). The organic layer was collected and washed with brine and dried over Na2SO4. Filtration and concentration in vacuo afforded yellow oil. In a 250 mL round bottom flask, the obtained yellow oil (6.45 g, 30 mmol) and anhydrous AlCl3 (12.02 g, 90 mmol) was mixed at 160 C for three hours. Reaction mixture was poured into ice water and concentrated hydrochloric acid solution was added to break complex formed during reaction.The mixture was taken in AcOEt (50 mL 3). The organic layer was combined and washed with water and brine, and dried over Na2SO4. After filtration and concentration in vacuo, the residues was purified by silica gel flash chromatography (PE/AcOEt 30:1) give (6) (4.74 g, 73.5%) as white solid.

The synthetic route of 35065-86-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gao, Hongping; Su, Ping; Shi, Yaling; Shen, Xiuxiu; Zhang, Yanmin; Dong, Jinyun; Zhang, Jie; European Journal of Medicinal Chemistry; vol. 90; (2015); p. 232 – 240;,
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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. 84228-44-4, name is Methyl 4-amino-3-chlorobenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 84228-44-4

A mixture of methyl 4-amino-3-chlorobenzoate (1.0 g, 5.4 mmol), n-pentyl nitrite (0.95 g, 8.1 mmol) and iodine (1.78 g, 7.0 mmol) was stirred under refluxing for 1 h. The mixture was diluted with methylene chloride (30 ml). The purple solution was washed with saturated sodium thiosulfate solution, brine, and dried over sodium sulfate. The title compound was obtained after flash column using EtOAc:hexane/2:98 as the eluant.

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 & CO., INC.; WO2007/79186; (2007); A2;,
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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. 13195-64-7, name is Diisopropyl malonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Diisopropyl malonate

(1) 200 mmol of diisopropyl malonate was reacted with 440 mmol of propargyl bromide plus 830 mmol of sodium hydride as a catalystInto 210mL anhydrous acetonitrile in ice water bath, stirring reaction for 8 hours, the product was washed with water, extracted with ethyl acetate, dried under reduced pressure to give the product as a brown solid, namely compound 1.

The synthetic route of 13195-64-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anhui Normal University; Hu Yimin; Fang Bo; (16 pag.)CN106946707; (2017); A;,
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Synthetic Route of 7335-27-5,Some common heterocyclic compound, 7335-27-5, name is Ethyl 4-chlorobenzoate, molecular formula is C9H9ClO2, 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: A mixture of substituted ethyl benzoate 2 (10 mmol) and hydrazinehydrate (20 mmol) in ethanol was stirred at room temperaturefor 3 h and then filtered. The crude product recrystallizedfrom absolute alcohol to give 3a-l, which were used directly forthe next step. Under this same condition, the intermediate compounds 8a-d were also prepared.

The synthetic route of 7335-27-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; He, Haifeng; Wang, Wei; Zhou, Yuan; Xia, Qin; Ren, Yanliang; Feng, Jiangtao; Peng, Hao; He, Hongwu; Feng, Lingling; Bioorganic and Medicinal Chemistry; vol. 24; 8; (2016); p. 1879 – 1888;,
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Application 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.

General procedure: To a stirred suspension of LiAlH4 (3.5 equiv.) in dry THF (1.0mL/mmol) under nitrogen atmosphere was slowly added a solution of the corresponding diethyl alkylpropanedioate (1 equiv.) in dry THF (1.0mL/mmol) at 0C. The reaction mixture was allowed to warm to rt and was then refluxed for 48h before being cooled to 0C. The reaction was quenched by careful addition of a saturated aqueous solution of NH4Cl until neutral or acidic pH. The precipitated aluminium salts were removed by filtration through a pad of Celite and washed with diethylether or a mixture of MeOH/CH2Cl2/Et2O 1:1:1. The organic phase of the filtrate was recovered, washed with water and brine, dried over MgSO4, filtered off and concentrated under reduced pressure to afford the corresponding crude product which was pure enough to be directly used in the next step.

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:
Article; Meguellati, Amel; Ahmed-Belkacem, Abdelhakim; Nurisso, Alessandra; Yi, Wei; Brillet, Rozenn; Berqouch, Nawel; Chavoutier, Laura; Fortune, Antoine; Pawlotsky, Jean-Michel; Boumendjel, Ahcene; Peuchmaur, Marine; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 217 – 229;,
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Adding a certain compound to certain chemical reactions, such as: 685-88-1, name is Diethyl fluoromalonate, 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 685-88-1, Formula: C7H11FO4

General Procedure: In a small vial, MBH carbonate 1a-e (0.25 mmol, 1 equiv), 2-fluoromalonate 2, (67 mg, 0.375 mmol, 1.5 equiv), and catalyst I (8 mg, 0.025 mmol, 10 mol %) in 1 mL of toluene were stirred at room temperature overnight. The crude mixture was monitored by 1H NMR and after completion the crude was purified by column chromatography, affording compound 3. 1,1-diethyl 3-methyl 1-fluoro-2-phenylbut-3-ene-1,1,3-tricarboxylate (3a):1H NMR (400 MHz, CDCl3) delta 7.31-7.28(m, 2H), 7.24-7.20(m, 2H), 6.37-6.37(m, 1H), 6.17(m, 1H), 5.08 (d, JH-F = 35.2 Hz, 1H), 4.24-4.22 (m, 2H), 4.03-4.02(m, 2H), 3.63(s, 3H), 1.24-1.22(t, J = 7.1 Hz, 3H), 1.03-1.02(t, J = 7.1 Hz, 3H). 13C NMR (100 MHz, CDCl3) delta 166.2, 165.2, 164.9, 164.8, 164.5, 138.1, 138.1, 134.9, 129.8, 129.8, 128.2, 127.8, 127.02, 126.9, 98.0, 95.9, 62.9, 62.7, 52.2, 49.0, 48.8, 13.8, 13.7; 19F NMR (376 MHz, CDCl3) delta -174.1 (d, J = 35.4 Hz). HRMS (ESI) calcd. for C18H25FNO6 (M+NH4)+, 370.1666 found 370.1665. Enantiomeric excess: 81%, -65.6 (CHCl3; c = 0.8 g/100 mL) determined by HPLC (Daicel Chiralpak IA, i-PrOH/Hexane = 5/95), UV 254 nm, flow rate 0.8 mL/min, major 9.7 min, minor 10.9 min.

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:
Article; Wang, Bing; Companyo, Xavier; Li, Jing; Moyano, Albert; Rios, Ramon; Tetrahedron Letters; vol. 53; 32; (2012); p. 4124 – 4129;,
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Adding a certain compound to certain chemical reactions, such as: 251458-15-8, name is Methyl 2-(3-bromophenyl)-2-methylpropanoate, 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 251458-15-8, Safety of Methyl 2-(3-bromophenyl)-2-methylpropanoate

Methyl 2-(3-bromophenyl)-2-methylpropanoate (Pharmabridge, Doylestown, Pa., USA (190 mg, 0.74 mmol), 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane) (206 mg, 0.81 mmol), [1,1?-bis(diphenylphosphino)ferrocene] dichloropalladium(II), complex with dichloromethane (27 mg, 0.04 mmol) and potassium acetate (217 mg, 2.22 mmol) were placed in a screw cap vial and flushed with a vacuum and argon cycle three times. Anhydrous 1,4-dioxane (4 mL) was added under argon and the resulting mixture was heated to 80 C. for 19 h. The reaction mixture was cool to RT and was diluted with ethyl acetate (20 mL). Celite (1 g) was added and filtered through a pad of celite. Solvents were removed under reduced pressure to afford the title compound which was used directly in the subsequent reaction.

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; Gilead Sciences, Inc.; Selcia Limited; Aciro, Caroline; Dean, David Kenneth; Dunbar, Neil Andrew; Highton, Adrian John; Jansa, Petr; Karki, Kapil Kumar; Keats, Andrew John; Lazarides, Linos; Mackman, Richard L.; Pettit, Simon N.; Poullennec, Karine G.; Schrier, Adam James; Siegel, Dustin; Steadman, Victoria Alexandra; (169 pag.)US2017/190737; (2017); A1;,
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14062-29-4, name is Ethyl 2-(3-chlorophenyl)acetate, 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: 14062-29-4

m-Chlorotoluene (1.89 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 m-chlorophenylacetate was obtained by column chromatography, in a yield of 83%. 1HNMR (400 MHz, CDCl3) delta 1.24 (t, J=7.2 Hz, 3H), 3.58 (s, 2H), 4.13 (q, J=7.2 Hz, 2H), 7.15-7.18 (m, 1H), 7.24-7.26 (m, 1H), 7.29 (s, 1H); 13CNMR (100 MHz, CDCl3) delta 14.2, 40.9, 61.1, 127.3, 127.5, 129.5, 129.8, 134.3, 135.9, 170.9; HRMS (ESI) calcd. for C10H11ClNaO2 [M+Na]: 221.0340. found: 221.0342. The ethyl m-chlorophenylacetate 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 m-chlorophenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 91%.

The synthetic route of 14062-29-4 has been constantly updated, and we look forward to future research findings.

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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Synthetic Route of 1000342-11-9, 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. 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1: Synthesis of methyl 5-bromo-3-(ethylamino)-2-methylbenzoate To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (1.0 g, 4.09 mmol) and acetaldehyde (180 mg, 4.09 mmol) in dichloroethane (10 mL), acetic acid (1.47 g, 24.58 mmol) was added and reaction stirred at room temperature for 30 minutes. Then sodium triacetoxyborohydride (2.6 g, 12.29 mmol) was added at 0 C., allowed to attain room temperature and stirring continued for 2 h. On completion, reaction mixture was diluted with dichloromethane, washed with water, saturated aqueous sodium bicarbonate solution and dried over sodium sulphate. Removal of the solvent under reduced pressure followed by column chromatographic purification afforded the desired compound (600 mg, 55%).

The synthetic route of Methyl 3-amino-5-bromo-2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KUNTZ, KEVIN W.; CHESWORTH, RICHARD; DUNCAN, KENNETH W.; KEILHACK, HEIKE; WARHOLIC, NATALIE; KLAUS, CHRISTINE; ZHENG, WANJUN; SEKI, MASASHI; SHIROTORI, SYUJI; KAWANO, SATOSHI; US2012/264734; (2012); A1;,
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