Tag: M.W=100-200

Some common heterocyclic compound, 2150-38-1, name is Methyl 3,4-dimethoxybenzoate, molecular formula is C10H12O4, 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. name: Methyl 3,4-dimethoxybenzoate

Example 1 Synthesis of 3,4-dimethoxy(4,4-dimethyl-3-oxopentanoyl)benzene In a 200 ml three-necked flask equipped with a mechanical stirrer, dropping funnel, reflux condenser, and a nitogen-inlet tube, 2.45 gm (61 mmol) of 60% sodium hydride, 10 gm (51 mmol) of methyl 3,4-dimethoxybenzoate, and 100 ml of anhydrous tetrahydrofuran were mixed with stirring under nitrogen stream, and refluxed with heating while 6.1 gm (61 mmol) of pinacolone was added dropwise. The refluxing under heat was continued for 7 hours. After cooling the reaction mixture, 30 ml of 2N hydrochloric acid was added and the mixture was extracted twice with chloroform. The extract was dried over anhydrous sodium sulfate and the solvent was removed by evaporation to give a crude product. Hexane was added to the crude product and insoluble substances were filtered off. The filtrate was concentrated by evaporation, and recrystallization afforded 8.9 gm of the target compound as colorless needles (yield: 65%). Melting Point: 52.3-53.3 C. IR(gammaKBr, cm-1): 1602, 1521, 1470, 1446, 1365, 1299, 1266, 1218, 1188, 1131, 885, 786, 729. 1 H-NMR(CDCl3, delta): 1.26(9 H, s, t-C4 H9), 3.95(3 H, s, OCH3), 3.96(3 H, s, OCH3), 6.24(1 H, s), 6.90(1 H, d, J=8.4 Hz), 7.49(1 H, s), 7.51(1 H, d, J=8.4 Hz). Elemental analysis: Calculated (%) C: 68.16, H: 7.63; Found (%) C: 68.23, H: 7.60.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2150-38-1, its application will become more common.

Reference:
Patent; Kao Corporation; US5146002; (1992); A;,
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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. 5048-82-8, name is Ethyl 3-(4-aminophenyl)acrylate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Ethyl 3-(4-aminophenyl)acrylate

The appropriate amino acid derivative from Example 9 (0.020 g, 0.05 mmol) was dissolved in DCM (1 mL). DMAP (0.018 g, 3 equivalents), Et3N (20 muL, 0.15 mmol, 3 equivalents), BroP (0.058 g, 0.15 mmol, 3 equivalent), and ethyl-4-aminocinnamate (0.029 g, 0.015 mmol, 3 equivalents) were added and the mixture stirred for 20 h at room temperature. Camphor-10-sulfonic acid (CSA; 0.046 g, 0.2 mmol, 4 equivalents) was added and the reaction mixture was stirred for an additional 24 h at room temperature.

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 5048-82-8.

Reference:
Patent; Boehringer Ingelheim (Canada) Ltd.; US2003/236251; (2003); 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. 5445-17-0, name is Methyl 2-bromopropanoate, A new synthetic method of this compound is introduced below., Recommanded Product: 5445-17-0

To a solution of E/Z mixture (5:1) of 2-propenylphenol (2.0 g, 14.9 mmol) in anhydrous DMF (30 mL) was added K2CO3 (2.68 g, 19.37 mmol) at 0 C. After stirring for 30 min at room temperature, methyl 2-bromopropionate (2.5 mL, 22.36 mmol) was added drop-wisely to the reaction mixture with a syringe. The reaction mixture was stirred for 10 h at room temperature, and poured into water (100 mL). The organic compounds were extracted with EtOAc (3 x 50 mL). The combined organic layer was washed with brine, dried (MgSO4), and concentrated under vacuum. Purification by silica gel chromatography (EtOAc/hexane=1/9, v/v) afforded the desired product as a colorless oil (3.34 g, 96%).

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:
Article; Lee, Sujin; Shin, Ju Yeon; Lee, Sang-Gi; Tetrahedron Letters; vol. 54; 7; (2013); p. 684 – 687;,
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These common heterocyclic compound, 140-11-4, name is Benzyl acetate, 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. Quality Control of Benzyl acetate

General procedure: Bioreactor cultures and biotransformations using E. coli JM109(pDTG601). Growth and biotransformation in the bioreactor usingE.coli JM109 (pDTG601) were carried out using a modification ofour previously published procedure.3b Thus, 5 mL of LB mediumsupplemented with ampicillin sodium salt (0.1 g/L) and glucose(5 g/L) were inoculated with a single colony of E. coli JM109(pDTG601), and grown overnight at 37 C and 150 rpm. Two500 mL shake-flasks containing 150 mL of MSB medium wereinoculated with 1 mL of the grown culture. These precultureflasks were placed in an orbital shaker at 37 C and 150 rpm, for12 hrs. Both entire cultures were used to inoculate the bioreactor(Sartorius Biostat A plus), charged with an initial volume of 2.5 L,and set to 500 rpm, 30 C, and air flow rate of 4L/min. The pHvalue was controlled automatically to 6.8 by addition of conc.ammonium hydroxide during the whole process. A pulse ofantifoam agents (Aldrich?s Antifoam Y: Silicone dispersion inwater 1:1) was added at the beginning of the run. At 6 h afterinoculation the dissolved oxygen value sharply increased(indicating carbon deprivation), whereupon a glucose fed-batchwas started by adding glucose (0.7 g/mL solution) from an initialrate of 0.08 mL/min to 0.54 mL/min in a 20 h period. When thebiomass concentration reached 15 g/L cdw, IPTG was added toinduce toluene dioxygenase expression (IPTG final concentrationin bioreactor of 10 mg/L), and the stirrer speed was set to900 rpm. After the culture reached the stationary phase (c.a.26 h, 50 g/L cdw aprox), glucose feeding was decreased to0.25 mL/min and substrate addition was started. A solution of thecorresponding substrate in liquid paraffin (0.5 M) was added at aflow rate of 20 mL/min using a peristaltic pump. After thebiotransformation was completed, the pH of the medium in thebioreactor was adjusted to 7.5. The culture broth was centrifugedat 7000 rpm and 4 C for 30 min, the supernatant was collectedand the cell pellet properly disposed. Centrifugation led to theseparation of the liquid paraffin (which contains no detectableamounts products) from the aqueous phase. The latter wasproperly lyophilized overnight to obtain a dry powder, whichwas extracted several times with ethyl acetate until no morediols were detected by TLC. The solvent was evaporated to affordthe corresponding diol, which was washed several times withhexanes to remove the liquid paraffin traces.

The synthetic route of Benzyl acetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pazos, Mariana; Martinez, Sebastian; Vila, Maria Agustina; Rodriguez, Paola; Veiga, Nicolas; Seoane, Gustavo; Carrera, Ignacio; Tetrahedron Asymmetry; vol. 26; 24; (2015); p. 1436 – 1447;,
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Reference of 15963-46-9, 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. 15963-46-9, name is Methyl 3-chlorocyclobutanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-(1-(pentan-3-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrazine (0.100 g, 0.311 mmol) and methyl 3-chlorocyclobutanecarboxylate (0.0925 g, 0.622 mmol) in DMF (1.56 mE, 0.311 mmol) was added cesium carbonate (0.203 g, 0.622 mmol) and the reaction mixture was stirred at 80 C for 5 hours. The reaction mixture was cooled to ambient temperature, diluted with water (15 mE) and stirred for 10 minutes. The reaction mixture was extracted with EtOAc and the combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (50% EtOAc/hexanes) to afford two isomers. Faster eluting peak: trans-methyl 3-(4-(4-(1-(pentan- 3 -yl)- 1 H-pyrazol-4-yl)pyrazolo [1 ,5-ajpyrazin-6-yl)- I H-pyrazol- 1 -yl)cyclobutanecarboxylate(28 mg, 21% yield) as an off-white foam. Slower eluting peak: cis-methyl 3-(4-(4-(1-(pentan- 3-yl)-l H-pyrazol-4-yl)pyrazolo [1 ,5-a]pyrazin-6-yl)- 1 H-pyrazol- 1 -yl)cyclobutanecarboxylate(58mg, 43% yield) as a thick 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 3-chlorocyclobutanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; CELGENE CORPORATION; ALLEN, Shelley; BOYS, Mark Laurence; CHICARELLI, Mark J.; FELL, Jay Bradford; FISCHER, John P.; GAUDINO, John; HICKEN, Erik James; HINKLIN, Ronald Jay; KRASER, Christopher F.; LAIRD, Ellen; ROBINSON, John E.; TANG, Tony P.; BURGESS, Laurence E.; RIEGER, Robert Andrew; PHENEGER, Jed; SATOH, Yoshitaka; LEFTHERIS, Katerina; RAHEJA, Raj K.; BENNETT, Brydon L.; (223 pag.)WO2016/90285; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 18595-12-5, name is Methyl 5-amino-2-methylbenzoate, 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 18595-12-5, Recommanded Product: 18595-12-5

Combine methyl 2-methyl-5-aminobenzoate (4.5 g, 27.2 mmol) and triethyl orthoformate (16.2 g, 109 mmol) in glacial acetic acid (25 mL). After 12 hours, add portionwise sodium azide (7.08 g, 109 mmol). Heat to 70 C. After 2 hours, cool the reaction mixture to ambient temperature, dilute with water (250 mL). Collect the solid by filtration, rinse with water, and dry to give methyl 2-methyl-5-(1H-tetrazol-1-yl)benzoate: Rf=0.13 (silica gel, ethyl acetate/hexane 1/4).

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; Maynard, George D.; Le, Tieu-Binh; US2001/34343; (2001); A1;; ; Patent; Aventis Pharmaceuticals Inc.; US6194406; (2001); B1;,
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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. 5164-76-1, name is Dimethyl pent-2-enedioate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C7H10O4

General procedure: The crude aryl diazonium tosylate 9 thus obtained was dissolved or suspended in MeOH (30 mL). Dimethyl glutaconate (1.45 mL, 10.0 mmol) and Pd(OAc)2 (112 mg, 0.5 mmol) were successively added while stirring. After stirring at r.t. for 15 h, the mixture was concentrated under reduced pressure and partitioned between CH2Cl2 (40 mL) and H2O (25 mL). The organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was briefly fractionated on SiO2 using CH2Cl2 or CH2Cl2- acetone (5:1) as eluent. Fractions containing arylation product were pooled and concentrated to give compound 10 of at least 90% purity (according to 1H NMR analysis). It was used in the next step without further purification.

The synthetic route of 5164-76-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dar’In, Dmitry; Kantin, Grigory; Bakulina, Olga; ?alubovskis, Raivis; Krasavin, Mikhail; Synthesis; vol. 51; 10; (2019); p. 2230 – 2236;,
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Related Products of 50413-30-4,Some common heterocyclic compound, 50413-30-4, name is Methyl 2-amino-4-methoxylbenzoate, molecular formula is C9H11NO3, 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.

Referential Example 23 3.1 mL of triethylamine and 1.3 mL of benzoyl chloride were added to 19 mL of methylene chloride solution containing 1.9 g of methyl 2-amino-4-methoxybenzoate while ice-cooled sequentially and stirred at room temperature for 3 hours. The solvent was evaporated under reduced pressure and chloroform and 1.0 mol/L hydrochloric acid were added to the obtained residue. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. Hexane and diisopropyl ether were added to the obtained residue and a solid substance was separated by filtration to obtain 2.6 g of methyl 2-(benzamido)-4-methoxybenzoate as white solid. 1H-NMR (CDCl3) delta: 3.92 (3H, s), 3.93 (3H, s), 6.65 (1H, dd, J = 9.0, 2.7 Hz), 7.51-7.59 (3H, m), 8.00 (1H, d, H = 9.0 Hz), 8.05-8.07 (2H, m), 8.63 (1H, d, J = 2.7 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-amino-4-methoxylbenzoate, its application will become more common.

Reference:
Patent; TOYAMA CHEMICAL CO., LTD.; EP1820795; (2007); A1;,
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Reference of 394-35-4, A common heterocyclic compound, 394-35-4, name is Methyl 2-fluorobenzoate, molecular formula is C8H7FO2, 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.

N-(Pyrrolidin-3-yl methyl)-2-(4-chlorophenyl)-4-methylthiazole-5-carboxamide (168 mg, 0.500 mmol) and methyl 2-fluorobenzoate (0.127 mL, 1.00 mmol) were dissolved in dimethylsulfoxide (4 mL). To this solution, potassium carbonate (138 mg, 1.00 mmol) and tetrabutylammonium iodide (18.5 mg, 0.0500 mmol) were added and the mixture was stirred at 140°C for 6 hours. Subsequently, the reaction mixture was allowed to cool and water was added. The mixture was then extracted with ethyl acetate and the extract was washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the resulting residue by silica gel column chromatography (hexane: ethyl acetate = 4:1 -> 2:1) gave 136 mg (58percent) of the desired compound as a colorless amorphous product. 1H NMR (400 MHz, CDCl3) delta 1.77-1.86 (1H, m), 2.11-2.19 (1H, m), 2.60-2.67 (1H, m), 2.71 (3H, s), 3.21-3.38 (4H, m), 3.54 (2H, t, J= 6.1 Hz), 3.87 (3H, s), 6.26 (1H, t, J = 6.1 Hz), 6.78 (1H, t, J = 7.9 Hz), 6.82 (1H, d, J = 8.6 Hz), 7.32-7.36 (1H, m), 7.41 (2H, d, J = 8.6 Hz), 7.63 (1H, dd, J = 1.8, 7.3 Hz), 7.85 (2H, d, J = 8.6 Hz). FAB+(m/z): 470 (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; KYORIN PHARMACEUTICAL CO., LTD.; EP1780210; (2007); A1;,
Ester – Wikipedia,
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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. 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Ethyl 2-ethoxy-2-iminoacetate

To a solution of cyclopropanecarbohydrazide (6.9 g, 69 mmol, 1 equiv) in ethanol (20mL) was added ethyl 2-ethoxy-2-iminoacetate (10 g, 69 mmol, 1 equiv). The mixture was stirred at 40C overnight. The resulting solid was filtered and the filter cake was washed with cool ethanol to afford ethyl 2-(2-(cyclopropanecarbonyl)hydrazinyl)-2- iminoacetate as a white solid, which was used for next step without further purification(5.8 g, 42.7% yield). LC-MS: m/z 200.1 (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 816-27-3.

Reference:
Patent; ANNAPURNA BIO INC.; TANG, Haifeng; BOYCE, Sarah; HANSON, Michael; NIE, Zhe; (213 pag.)WO2019/169193; (2019); A1;,
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