Tag: M.W=200-300

252881-74-6, 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. 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, A new synthetic method of this compound is introduced below.

A solution of 4-[4-(3,5-dioxo-hexyl)-phenylcarbamoyl]-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester (1.5 g, 3.6 mmol), 3-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester (1.0 g, 3.6 mmol) and DIEA (1.3 muL, 7.2 mmol) in CH2Cl2 (10 mL) was stirred at rt overnight. The solvent was removed in vacuo and the residual oil purified using column chromatography EtOAc/MeOH (95:5) to give the title compound as a transparent oil, (M+1)=579.

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; Bradshaw, Curt; Bhat, Abhijit; Lai, Jing Yu; Doppalapudi, Venkata; US2008/166364; (2008); A1;,
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59247-47-1, Adding some certain compound to certain chemical reactions, such as: 59247-47-1, name is tert-Butyl 4-bromobenzoate, 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 59247-47-1.

Example 30 Preparation of 4-((S)-3-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenoxy}-pyrrolidin-1-yl)-benzoic acid To a mixture of 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid [4-((S)-pyrrolidin-3-yloxy)-phenyl]-amide hydrochloride (180 mg, 0.37 mmol), 4-bromobenzoic acid tert-butyl ester (114 mg, 0.44 mmol), sodium tert-butoxide (118 mg, 1.23 mmol) and (2′,4′,6′-triisopropyl-1,1′-biphenyl-2-yl)dicyclohexylphosphine (X-PHOS, 40 mg) in dioxane (5 mL) bubbled with argon was added tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (24 mg). The mixture was heated at 105¡ã C. for 2 hrs. Solvents were evaporated and the residue was extracted with ethyl acetate and 0.1N hydrochloric acid. The organic layer was dried and concentrated. The residue was purified through ISCO column chromatography (silica gel, ethyl acetate in hexane, 5percent to 60percent linear gradient) to give a white solid as 4-((S)-3-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenoxy}-pyrrolidin-1-yl)-benzoic acid tert-butyl ester (150 mg, yield 69percent). The above 4-((S)-3-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenoxy}-pyrrolidin-1-yl)-benzoic acid tert-butyl ester (150 mg) was dissolved in a mixture of methylene chloride (2 mL) and trifluoroacetic acid (4 mL). The mixture was stirred at room temperature for 1 hr and solvents were evaporated. The residue was extracted with ethyl acetate and water. The organic layer was dried and solvents were evaporated. The residue was triturated with ethyl acetate and hexanes to give a tan solid as 4-((S)-3-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenoxy}-pyrrolidin-1-yl)-benzoic acid (75 mg). LC-MS for C28H22F3N3O5 (m/e) calcd 537, obsd 538 (M+H).

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 59247-47-1.

Reference:
Patent; Bolin, David Robert; Cheung, Adrian Wai-Hing; Firooznia, Fariborz; Marcopulos, Nicholas; Qian, Yimin; US2010/152445; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

17100-63-9, A common compound: 17100-63-9, name is Methyl 4-bromo-3-methoxybenzoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

To a solution of methyl 4-iodo-3-methoxybenzoate (9) (0.5 g, 1.71 mmol) and tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate(0.70 g, 2.05 mmol) in 1,4-dioxane (10.0 mL) was added 2.0 mL of water. The reaction mixture was degassed with argon for about30 min. After that Pd(dppf)Cl2.DCM (0.069 g, 0.085 mmol) andNa2CO3 (0.36 g, 3.42 mmol) were added to the reaction mixture andagain degassed with argon for another 20 min. The reactionmixturewas stirred under reflux for 3 h. After cooled down to roomtemperature, the mixture was extracted with EtOAc, washed withbrine, dried over Na2SO4, and concentrated under reduced pressure.The crude product was purified by column chromatography(Hexane/EtOAc 4:6) to afford 10 as a yellow solid (0.52 g, 79.7%).1H NMR (500 MHz, CDCl3) delta 8.15 (d, J 5.0 Hz, 1H), 7.85 (s, 1H), 7.65(d, J 10.0 Hz, 2H), 7.56 (d, J 10.0 Hz, 2H), 7.32 (d, J 10.0 Hz, 1H),7.28 (s, 1H), 3.86 (s, 3H), 3.82 (s, 3H), 1.62 (s, 9H).

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 4-bromo-3-methoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Naik, Ravi; Valentine, Heather; Hall, Andrew; Mathews, William B.; Harris, James C.; Carter, C. Sue; Dannals, Robert F.; Wong, Dean F.; Horti, Andrew G.; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 644 – 656;,
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541-16-2, Adding some certain compound to certain chemical reactions, such as: 541-16-2, name is Di-tert-Butyl malonate, 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 541-16-2.

General procedure: alpha,beta-Unsaturated aldehyde (3.0 mmol) and malonate (3.0 mmol) were added into asolution of TiCl4 (6.0 mmol) in CCl4 (2.0 mL) and THF (10 mL) at 0 C, Then, pyridine (0.96 mL, 12.0 mmol) in THF (2 mL) was added dropwisely over 1 h. The resulting mixture was stirred at room temperature overnight. After quenched with water, the mixture was extracted with ethyl acetate, dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography with hexane/ethyl acetate = 20/1 to afford the product.

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 541-16-2.

Reference:
Article; Wei, Xu; Lu, Junzhu; Duan, Wei-Liang; Synthesis; vol. 48; 23; (2016); p. 4155 – 4160;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 110661-91-1 name is tert-Butyl 4-bromobutanoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 110661-91-1

Methyl 3-(4-(tert-butoxy)-4-oxobutoxy)beiizoate A solution of methyl 3Thydroxybenzoate (commercially available from for example Aldrich) (1 g, 6.6 mmol) and K2C03 (1.82 g, 13.2 mmol) in DMF (10 mL) was treated with tert-butyl 4-bromobutanoate (commercially available from for example Aldrich) (2.2 g, 9.9 mmol) and the mixture was stirred at 60 C for 16 hours. A further aliquot of K2C03 (1.82 g, 13.2 mmol) and tert-butyl 4-bromobutanoate (2.2 g, 9.9 mmol) were added and the mixture was heated at 60 C for further 6 hours. The mixture was cooled to ambient temperature and partitioned between ethyl acetate (50 mL) and water (50 mL). The organic phase was washed with brine (2 x 50 mL), dried (hydrophobic frit) and evaporated to dryness. The product was purified by chromatography on silica using a gradient elution from 0% to 100% methyl tert-butyl ether in cyclohexane to afford the title compound (1.4 g, 4.8 mmol, 72 % yield). LCMS RT= 1.26 min, ES+ve m/z 312 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 4-bromobutanoate, and friends who are interested can also refer to it.

Reference:
Patent; YALE UNIVERSITY; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CAMBRIDGE ENTERPRISE LIMITED UNIVERSITY OF CAMBRIDGE; CREWS, Craig, M.; BUCKLEY, Dennis; CIULLI, Alessio; JORGENSEN, William; GAREISS, Peter, C.; MOLLE, Inge, Van; GUSTAFSON, Jeffrey; TAE, Hyun-Seop; MICHEL, Julien; HOYER, Dentin, Wade; ROTH, Anke, G.; HARLING, John, David; SMITH, Ian Edward, David; MIAH, Afjal, Hussain; CAMPOS, Sebastian, Andre; LE, Joelle; WO2013/106646; (2013); A2;,
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Ester – an overview | ScienceDirect Topics

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. 23877-12-5, name is tert-Butyl 2-bromo-2-methylpropanoate, This compound has unique chemical properties. The synthetic route is as follows., 23877-12-5

Step 2: 1-[4-methylthiophenyl]-(E)-3-[3,5-dimethyl-4-tertiobutylcarbonyldimethylmethyloxyhenyl]prop-2-en-1-one (Intermediate 2) Caesium carbonate (87 g, 0.134 mol, 4 eq) and tetrabutylammonium iodide (12 g, 0.033 mol, 0.5 eq) are added to an intermediate solution 1 (20 g, 0.067 mol, 1 eq) in 50 ml of a DMSO/water mixture (3/2). The reaction medium is stirred for 30 minutes at 80 C. and tert-butyl bromoisobutyrate (30 g, 0.134 mol, 2 eq) is added. Then 2 additions of 2 eq of tert-butyl bromoisobutyrate diluted to 50% in DMSO are each made at an interval of 1 hour. The reaction medium is stirred for 2 days at 80 C. The reaction medium is left to cool to ambient temperature and then 1.5 litres of water are added and the product is extracted with dichloromethane (4 times). The organic phase is dried on a phase-separation cartridge and evaporated dry. Purification on silica gel (cyclohexane/ethylacetate: 95/5 to 80/20): 18 g (orange solid, yield: 61%).

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; NASHPHARM; LARUELLE, Claude; BONNAFOUS, Ludovic; US2020/23067; (2020); 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 541-16-2 as follows. 541-16-2

General procedure: alpha,beta-Unsaturated aldehyde (3.0 mmol) and malonate (3.0 mmol) were added into asolution of TiCl4 (6.0 mmol) in CCl4 (2.0 mL) and THF (10 mL) at 0 C, Then, pyridine (0.96 mL, 12.0 mmol) in THF (2 mL) was added dropwisely over 1 h. The resulting mixture was stirred at room temperature overnight. After quenched with water, the mixture was extracted with ethyl acetate, dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography with hexane/ethyl acetate = 20/1 to afford the product.

According to the analysis of related databases, 541-16-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wei, Xu; Lu, Junzhu; Duan, Wei-Liang; Synthesis; vol. 48; 23; (2016); p. 4155 – 4160;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

87-13-8, Name is Diethyl 2-(ethoxymethylene)malonate, 87-13-8, 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.

A mixture of aniline (25.6 g, 0.28 mol) and diethyl 2-(ethoxymethylene)malonate (62.4 g, 0.29 mol) was heated at 140-150 C. for 2 h. The mixture was cooled to room temperature and dried under reduced pressure to afford 2-phenylaminomethylene-malonic acid diethyl ester as a solid, which was used in the next step without further purification. 1H NMR (d-DMSO) delta 11.00 (d, 1H), 8.54 (d, J=13.6 Hz, 1H), 7.36-7.39 (m, 2H), 7.13-7.17 (m, 3H), 4.17-4.33 (m, 4H), 1.18-1.40 (m, 6H).

Statistics shows that Diethyl 2-(ethoxymethylene)malonate is playing an increasingly important role. we look forward to future research findings about 87-13-8.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; US2012/309758; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

59247-47-1, These common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-bromobenzoate, 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 50-mL round-bottom flask was added (1 S,4S,.5R)-.5-[[5-cyclopropyl-3-(2,6-dichlorophenyl)- L2-oxazol-4-yl]methoxy]-2-azabicyclo[2.2.1 ]heptane 12d (800 mg, 2.11mmol, 1.0 equiv.), tert-buty 4-bromobenzoate 52b (650 mg, 2.53 mmol, 1.20 equiv.),Pd2(dba)3 (190 mg, 0.21 mmol, 0.10 equiv.), BINAP (130 mg, 0.21 mmol, 0.10 equiv),Cs2C01 (960 mg, 2.9.5 mmoL 1.40 equiv.), and toluene (.5 mL) and the resulting mixture was20 stirred at 110 ¡ãC overnight. After cooling to room temperature, l 00 mL of I-hO v.¡¤as addedand the aqueous mixture was extracted with ethyl acetate (l 00 mL x 2). Tiw combinedorganic extracts were washed with brine (100 mL x 2), dried over anbydrous sodium sulfate,filtered, and concentrated under reduced pressure. The residue was purified by silica gelcolumn chromatography eluting vvith ethyl acetate/petroleum ether (1 :6) to give 0.55 g (4Tpercent)25 of tert-buiyl 4-[(1 S,4S,5R)-.5-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-l ,2-oxazol-4-yl]methoxy ]-2-azabicyclo[2.2.1 ]heptan-2-yl]benzoate 52c as a light green solid.

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 59247-47-1.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); 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 99548-54-6 as follows. 99548-54-6

A solution of methyl 3-bromo-2-methylbenzoate (from for example AstaTech, 24.35 g, 106 mmol) in benzene (300 mL) was treated with N-bromosuccinimide (22.7 g, 128 mmol) followed by benzoyl peroxide, 95% (1.3 g, 5.35 mmol). The reaction mixture was flushed with nitrogen and kept under nitrogen. The reaction mixture was heated at 80C for 2 days. The reaction mixture was concentrated under reduced pressure and treated with hexanes (200 mL). The resulting solids were filtered off, washed with hexanes then with 25% EtOAc / hexanes. The filtrate was concentrated under reduced pressure and the residue was absorbed directly onto silica gel. The product was purified by chromatography (ISCOCombiflash, 330 g, 200 ml/min, 0-8.7% EtOAc / Hexanes over 30 minutes) to yield the title compound (32.4 g, 105 mmol, 99% yield) as an orange liquid. LC/MS: RT= 1.13 min, m/z = 226.8/228.9.

According to the analysis of related databases, 99548-54-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; HARLING, John David; NEIPP, Christopher E.; PENDRAK, Israil; SMITH, Ian Edward David; TERRELL, Lamont Roscoe; YOUNGMAN, Mark; (120 pag.)WO2017/46036; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics