Tag: M.W=100-200

Synthetic Route of 711-01-3,Some common heterocyclic compound, 711-01-3, name is Methyl adamantane-1-carboxylate, molecular formula is C12H18O2, 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 flame-dried round bottom flaskcharged with 40 mmol (4.0 equiv) of 4-bromoanisole in 40 mL THF was cooled to?78 °C and 16 mL BuLi (2.5 M in hexane, 40 mmol, 4.0 equiv) was added dropwisevia syringe. The mixture was stirred for 1.5 h at ?78 °C before the addition of thecorresponding methyl ester (10 mmol, 1.0 equiv), then the mixture was warmed toroom temperature and stirred overnight. After ammonium chloride solutionquenching, the precipitated solid was removed by filtration. The filtrate was extractedwith ethyl acetate (3 × 30 mL), washed with sodium chloride solution, and dried overNa2SO4. After filtration and concentration, the residue was purified by columnchromatography to afford the tertiary alcohol as a white solid.

The synthetic route of 711-01-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pan, Yue; Jia, Kunfang; Chen, Yali; Chen, Yiyun; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 1215 – 1221;,
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Adding a certain compound to certain chemical reactions, such as: 23426-63-3, name is Methyl 2-bromo-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 23426-63-3, Application In Synthesis of Methyl 2-bromo-2-methylpropanoate

To a solution of 3-methyi-4- mtro-lH-pyrazole (40 g, 314.71 mmol) in DMF (700 mL) was added NaH (18.88 g, 472.06 mmol, 60% purity) at 0 C over a period of 30 min under N2. The reaction was then stirred at 25 C for 2 h followed by the addition of methyl 2-bromo-2-methylpropanoate (85.46 g, 472.06 mmol, 61.04 mL) dropwise at 0C. The reaction mixture was warmed to 25 C and stirred at 25 C for another 16 h. TLC (petroleum ether/ethyl acetate = 5: 1) showed the starting material was consumed completely. The reaction was quenched by ice water slowly and then extracted with EtOAc (3 chi 700 mL). The combined organic phase was washed with brine (3 chi 200 mL), dried over anhydrous Na2S(, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 30: 1- 15: 1), to yield the desired product as a light yellow solid. H NMR (400 MHz, C DC M: 5 8.29 (s, 1 H), 3.72 is. 1 1 1). 2.51 (s, I H), 1 .84 (s, 6 H).

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-bromo-2-methylpropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DENALI THERAPEUTICS INC.; ESTRADA, Anthony A.; FENG, Jianwen A.; LYSSIKATOS, Joseph P.; SWEENEY, Zachary K.; DE VICENTE FIDALGO, Javier; (271 pag.)WO2017/87905; (2017); A1;,
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Reference of 13671-00-6, A common heterocyclic compound, 13671-00-6, name is Methyl 2,6-difluorobenzoate, molecular formula is C8H6F2O2, 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.

To a solution of compound 1 (21.0 g, 122.0 mmol) in concentrated sulfuric acid (50 mL) was added fuming nitric acid (8 mL) dropwise at 0 C. After the reaction mixture was stirred at 0 C for 1 h, it was poured into ice-water. The precipitate was collected by filtration and rinsed with water to give 2 (26.0 g, 98%) as a white solid, mp 58-60 C. 1H NMR (CDCl3): delta 8.25-8.22 (m, 1H), 7.15-7.11 (m, 1H), 4.01 (s, 3H).

The synthetic route of 13671-00-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Min; Gao, Mingzhang; Miller, Kathy D.; Zheng, Qi-Huang; Bioorganic and Medicinal Chemistry Letters; vol. 23; 4; (2013); p. 1017 – 1021;,
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Adding a certain compound to certain chemical reactions, such as: 4720-83-6, name is 6-Oxabicyclo[3.2.1]oct-3-en-7-one, 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 4720-83-6, HPLC of Formula: C7H8O2

Step 3: To a stirred solution of alkene intermediate (1 .68 g, 13.50 mmol, 1 equiv.) in dry THF (70 mL), was added dropwise lithium aluminum hydride (1 M in THF, 20 ml_, 20 mmol, 1 .5 equiv.) at 0C under azote atmosphere. The reaction mixture was kept at 0C for 1 hours. Then, water (2 ml_), 15% aqueous sodium hydroxide (2 mL) and water (5 mL) were successively added, and the mixture was allowed to warm to room temperature and stirred for 2h30. The salts were filtered through a pad of celite and the filtrate was dried over Na2S04 and concentrated under vacuum to yield (1 S,5S)-5-(hydroxymethyl)cyclohex-2-en-1 -ol (1 .87 g, quant.) as a colorless 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, 6-Oxabicyclo[3.2.1]oct-3-en-7-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BCI PHARMA; SURLERAUX, Dominique; AMIABLE, Claire; GUILLON, Remi; (239 pag.)WO2017/191297; (2017); 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. 10601-80-6, name is Ethyl 3,3-diethoxypropionate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Ethyl 3,3-diethoxypropionate

General procedure: 2-aminopyridine 1a (47 mg, 0.5 mmol), ethyl 3,3-diethoxypropanoate 2 (285 mg, 1.5 mmol) and p-TsOH (8.6 mg, 10 mol %) were stirred in 2 mL of toluene for 6 h at 80 C. After completion of the reaction (monitored by TLC), the water (10 mL) was added. The aqueous solution was extracted with ethyl acetate (3×8 mL) and the combined extract was dried with anhydrous MgSO4. The solvent was removed and the crude product was separated by column chromatography (eluted with petroleum ether/ethyl acetate = 2:1) to give a pure sample of 3a (Yellow crystal, 100 mg, 82%).

According to the analysis of related databases, 10601-80-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Wenjie; Wang, Shaohua; Zhan, Haiying; Li, Mingshan; Synlett; vol. 25; 10; (2014); p. 1478 – 1481;,
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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. 6290-49-9, name is Methyl 2-methoxyacetate, A new synthetic method of this compound is introduced below., COA of Formula: C4H8O3

Intermediate 51 l-(5-Fruoropyridin-2-yl)-2-methoxyethanoneTo a solution of 2-bromo-5-fluoropyridine (15.0 g, 85.23 mmol) in methyl t-butyl ether (250 ml) at -78 0C was added tert-butyllithium (60.2 ml, 102.28 mmol) with caution.After the addition of the organolithium was completed, the resulting black solution was stirred at-78 0C for 15 minutes whereupon methyl 2-methoxyacetate (8.43 ml, 85.23 mmol) in 10 mlMTBE was added to the solution. The mixture was stirred for 3 hours at -78 0C whereupon saturated NH4Cl was added in order to quench the reaction.The mixture was partitioned between EtOAc and brine and the organic extract was dried and evaporated under reduced pressure. Purification by column chromatography (20% ->40%EtOAc/hexanes) gave the titled compound as a yellowish solid 6.19 g (43% yield). LCMS: 170[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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/132502; (2008); A1;,
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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 18595-14-7 as follows. Recommanded Product: Methyl 4-amino-3-methylbenzoate

To a 500 mL round-bottom flask was added methyl 4-amino-3-methylbenzoate A-6a (10.0 g, 60.54 mmol, 1.0 equiv.), AcOH (200 mL), and NaSCN (19.6 g, 4.0 equiv.), followed by the dropwise addition of bromine (9.7 g, 60.70 mmol, 1.0 equiv.) in AcOH (100 mL) at 0 C. The resulting mixture was stirred at 30 C for 16 h and then quenched with ice water (500 mL), The pH value of the solution was adjusted to 9 using sodium hydroxide. The aqueous mixture was extracted with ethyl acetate (500 mL x 3), and the combined organic layers were washed with brine (500 mL x 3), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford methyl 2-amino-4-methyl-l,3-benzothiazole-6-carboxylate A-6b (15 g) as a yellow solid. The product was carried on to the next step without further purification.

According to the analysis of related databases, 18595-14-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (249 pag.)WO2018/39384; (2018); 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. 18595-18-1, name is Methyl 3-amino-4-methylbenzoate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 3-amino-4-methylbenzoate

Step 1: synthesis of methyl 3-(7-aminothieno[2,3-b]pyrazine-6-carboxamido)-4-methylbenzoate (108) A solution of 7-aminothieno[2,3-b]pyrazine-6-carboxylic acid (8) (2.56 mmol, 500 mg), methyl 3-amino-4-methylbenzoate (2.56 mmol, 423 mg), TBTU (3.84 mmol, 1234 mg) and DIPEA (7.68 mmol, 1.260 mL in DMF (10 mL) was stirred 2 days at 80 C. The brown solution was poured into citric acid solution, the precipitation was filtered of and washed with water. Purification by chromatography (0-40% ethyl acetate in CH2Cl2) gave methyl 3-(7-aminothieno[2,3-b]pyrazine-6-carboxamido)-4-methylbenzoate 108 (143 mg, 15%). (m/z)=343 (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; Folmer, Brigitte Johanna Bernita; Man, de Adrianus Petrus Antonius; Gernette, Elisabeth Sophia; Corte Real Goncalves Azevedo, Rita; Ibrahim, Hemen; US2013/79341; (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. 3196-15-4, name is Methyl 2-bromobutyrate, A new synthetic method of this compound is introduced below., Formula: C5H9BrO2

Weighed 2,4-dichlorophenol (815mg, 5mmol) in 100mL round bottom flask was added anhydrous potassium carbonate (1.38g, 10.0mmol, 2eq), acetone (30 mL) and 2-bromo-butyric acid methyl ester ( 995.6mg, 5.5mmol, 1.1eq), was heated under reflux for 12 hours.The reaction was cooled to room temperature, the solid was removed by suction filtration, and the filtrate was evaporated to dryness after the addition of water (30 mL), extracted with ethyl acetate (50mL × 3), combined extracts were washed with water (20mL × 2) and saturated brine (20 mL ) was washed, dried over anhydrous sodium sulfate, filtered and concentrated, the crude product was purified by silica gel column chromatography [V (ethyl acetate) :V (petroleum ether) = 1: 8] to give 1.22g, 93% yield.1HNMR (400MHz, CDCl3)

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; Changzhou University; Chen, Xi; Liang, Cuirong; Yang, Qinghong; Ren, Jie; Jin, Guihua; Huang, Qianhui; Xu, Yuanyuan; Hu, Kun; (32 pag.)CN105440020; (2016); A;,
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These common heterocyclic compound, 2033-24-1, name is 2,2-Dimethyl-1,3-dioxane-4,6-dione, 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. category: esters-buliding-blocks

General procedure: Method A: Adapted from the procedure of Srensen et al.14 To a solution of Meldrum?s acid (1equiv) in dichloromethane at 0C was added pyridine (2equiv) drop wise, and the resulting solution was stirred for 15min. The corresponding acid chloride (1equiv) was added to this reaction mixture. Thereafter, the reaction was stirred for 1.5h at 0C, and for an additional 1.5h at room temperature. The reaction was quenched with 2M hydrochloric acid, and extracted with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography using a gradient from 5% to 10% ethyl acetate in hexane, 1% acetic acid to yield acyl Meldrum?s acids (11a-e, j, l, p).

The synthetic route of 2,2-Dimethyl-1,3-dioxane-4,6-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Verma, Astha; Wong, Dawn M.; Islam, Rafique; Tong, Fan; Ghavami, Maryam; Mutunga, James M.; Slebodnick, Carla; Li, Jianyong; Viayna, Elisabet; Lam, Polo C.-H.; Totrov, Maxim M.; Bloomquist, Jeffrey R.; Carlier, Paul R.; Bioorganic and Medicinal Chemistry; vol. 23; 6; (2015); p. 1321 – 1340;,
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