Author: Jessica.F

Synthetic Route of 1128-00-3, These common heterocyclic compound, 1128-00-3, name is Ethyl 2-aminocyclohex-1-enecarboxylate, 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.

In a 2000 ml flask were charged ethyl 2-aminocyclohexene-1-carboxylate (80.0 g, 472.8 mmol), pyridine (37.4 g, 472.8 mmol), and acetonitrile (190 ml), and the mixture was dissolved by heating to 40 C. While keeping the mixture at 40-50 C., a solution (126 ml) of benzyl chloride (63.14 g, 449.2 mmol) in acetonitrile was added dropwise. The mixture was stirred at 50-60 C. for 1.5 hr, cooled, and water (631 ml) was added dropwise at 20-30 C. over 30 min. After stirring at the same temperature for 30 min, the precipitate was collected by filtration and washed with water (631 ml). The obtained powder was dried under reduced pressure at 60 C. yield 119.62 g, 97%. [0533] Anal. calcd. for C16H19NO3, C, 70.31; H, 7.01; N, 5.12. found C, 70.29; H, 7.15; N, 5.08. HR-Ms calcd. for C16H19NO3, 274.1438 ([M+H]+). found, 274.1428 ([M+H]+).

The synthetic route of 1128-00-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yamano, Mitsuhisa; Yamada, Masatoshi; Usutani, Hirotsugu; US2015/51416; (2015); A1;,
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Synthetic Route of 1865-29-8, 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. 1865-29-8, name is Methyl 2-phenylacrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Add Cu (OAc) 2 · H2O (2.0mg) to a dry reaction flask replaced with nitrogen(R) -L4 (Ar ‘= 4-Me-3,5- (t-Bu) 2-Ph) (5.6 mg), toluene (2.0 mL), and stirred at room temperature until a blue solution.Reduce the temperature to -25 , add Poly(methylhydrosiloxane) (120muL) and tert-butanol (182muL) to the above liquid,After stirring for 5 min, methyl 2-phenylacrylate (161 mg) was added.After stirring for 2h, then add saturated NH4Cl solution (4.0mL), continue stirring for 30min, and then separate the liquid,The aqueous phase was extracted with ethyl acetate (3 × 5.0 mL), and the combined organic phase was washed with saturated NaCl solution,The product was dried, concentrated and separated by anhydrous sodium sulfate (149mg, yield 91%, ee 35%,The dominant configuration is (S) -configuration.

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

Reference:
Patent; Dalian University; Li Zhengning; Zhao Xiaoyuan; Bai Rui; Li Quancheng; Jiang Lan; (11 pag.)CN110903189; (2020); A;,
Ester – Wikipedia,
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Related Products of 1014645-87-4, 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. 1014645-87-4 name is Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride, 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.

To a solution of 2,5-dichloronicotinic acid (1.84 g, 7.06 mmol) in dry dimethylformamide (15 ml) 1-Hydroxybenzotriazole hydrate (1.08 g, 7.06 mmol) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (2.03 g, 10.58 mmol), a solution of methyl 4-(1-aminocyclopropyl)benzoate hydrochloride (D7) (1.67 g, 7.06 mmol) and triethylamine (0.98 ml, 7.06 mmol) in dry dimethylformamide (15 ml) was added and the resulting mixture was stirred 1 h at room temperature. NH4Cl saturated solution (50 ml) was added the mixture was extracted with ethylacetate (3×50 ml). Collected organics, after solvent evaporation, was purified by Biotage column SNAP-Si (50g) eluting with a mixture dichloromethane/ethylacetate from 100/0 to 95:5. Collected organics after solvent evaporation afforded the title compound (D97) (1.03 mg)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Borriello, Manuela; Rovati, Lucio; Stasi, Luigi Piero; Buzzi, Benedetta; Colace, Fabrizio; US2013/261100; (2013); 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 35598-05-1 as follows. name: Methyl 4-methoxy-2-methylbenzoate

To a solution of methyl o-methylbenzoate (1.00 equiv) in CHCl3 (2-5 mL per mmol of methyl o-methylbenzoate) or CCl4 (5 mL per mmol of methyl o-methylbenzoate) was added NBS(1.10-2.20 equiv) and AIBN (0.02-0.04 equiv). The reaction was refluxed for 2-22 h before being cooled to rt. The solvent was then removed in vacuo (CHCl3 solvent) or via distillation (CCl4 solvent) within a fumehood to afford the desired brominated compound. CAUTION: CHCl3 and especially CCl4 are extremely toxic and carcinogenic and thus must be handled cautiously with gloves and within a fumehood appropriately ventilated.

According to the analysis of related databases, 35598-05-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; D’Hollander, Agathe C.A.; Westwood, Nicholas J.; Tetrahedron; vol. 74; 2; (2018); p. 224 – 239;,
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Reference 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.

Example 724: 2-(2-cyclopropylmethoxy-5-fluoro-4′-trifluoromethyl-biphenyl-4-yl)-4- methyl-pentanoic acid. Step lDiethyl 2-(2,5-difluoro-4-nitrophenyl)-2-isobutylmalonate2-Isobutylmalonic acid diethyl ester (40.Og, 0.185 mol) in DMF (5OmL) was added dropwise to a stirred suspension of sodium hydride (60% in mineral oil, 8.0g, 0.33 mol) in 200 mL DMF (20OmL) over 20 min. at O0C under nitrogen. The mixture was stirred for 0.5 h at room temperature, cooled to 0 C and l,2,4-trifluoro-5-nitro-benzene (30.0g, 169.5 mmol) in DMF (15OmL) was added dropwise. The resulting reaction mixture was stirred at room temperature for 16h, poured into ice water (20OmL) and extracted with EtOAc (3x10OmL). The combined organic phases were washed with water (3x10OmL), brine (10OmL) and dried (MgStheta4). Evaporation of solvent under reduced pressure gave a brown oil which was purified by column chromatography over silica gel (Heptane-EtOAc, gradient) to give 57.0 g (90%) of 2-(2,5- difluoro-4-nitrophenyl)-2-isobutylmalonic acid diethyl ester as yellow oil. H NMR (300 MHz, CDCVTMS): delta 7.87 (dd, J = 12.3, 6.0 Hz, IH), 7.79 (dd, J = 10.1, 6.4 Hz, IH), 4.30^1.18 (m, 4H), 2.27 (d, J = 5.8 Hz, 2H), 1.60-1.50 (m, IH), 1.26 (t, J = 7.1 Hz, 6H), 0.82 (d, J = 7.0 Hz, 6H); 13C NMR (75 MHz, CDCI3/TMS): delta 168.2, 155.1 (d, 1JcF = 252.3 Hz), 150.9 (d, 1JcF = 263.2 Hz), 135.7, 135.1, 120.0 (dd, 2JCF = 26.0, 3JCF = 4.0 Hz), 113.0 (d, 2JCF = 29.0 Hz), 62.3, 43.1, 24.9, 23.8, 13.8.

The synthetic route of 10203-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; WO2009/86277; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 121-98-2, A common heterocyclic compound, 121-98-2, name is Methyl 4-methoxybenzoate, molecular formula is C9H10O3, 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.

General procedure: A mixture of methyl benzoates (15.0 mmol), CH3OH (30.0 mL) wereplaced in a 100mL round-bottomed flask equipped with a magnetic stirrer.Stirring for 10 minutes in 0 C. Then hydrazine hydrate (4.0 eq.) was added to the flask. Afterword the mixture was stirred under reflux 8 h, the reaction system was concentrated to remove CH3OH and most of hydrazine hydrate. After cooling, the contents were added petroleum-ether (50 mL) by stirring, then the white solids would be separated, washed with water and dried under vacuum. The yield was 65%~80%.

The synthetic route of 121-98-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Guofu; Yu, Yidong; Zhao, Yiyong; Xie, Xiaoqiang; Ding, Chengrong; Synlett; vol. 28; 11; (2017); p. 1373 – 1377;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 7270-63-5, name is 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H6N2O4

General procedure: Rh/Au catalyzed (but-3-yn-1-yl)-aniline trapping with diazos: To a 4.0 mL vial equipped with a magnetic stir bar was added Rh2(esp)2 (1 mol %), PPh3AuCl (10 mol %), and AgSbF6 (10 mol %) directly into the reaction vessel. A solution of (but-3-yn-1-yl)-aniline (1.1 equiv.) was then added. Lastly, the diazo (1.0 equiv.) was added. The reaction vessel was sealed and allowed to stir at reflux for 16 h (Take caution when opening reaction flask. Evolution of N2 gas creates pressurized system.) After this time, the crude reaction mixture was filtered through a slurry of celite/silica gel, concentrated, and analyzed via crude 1H NMR. The crude mixture was then purified via flash chromatography to furnish functionalized spiropyrrolidines.

The synthetic route of 7270-63-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hunter, Arianne C.; Almutwalli, Bilal; Bain, Anae I.; Sharma, Indrajeet; Tetrahedron; vol. 74; 38; (2018); p. 5451 – 5457;,
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Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 29823-21-0, name is Ethyl 8-Bromooctanoate, 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. COA of Formula: C10H19BrO2

General procedure: 2,6-dichloro-9H-purine (5 mmol) or intermediates 5 was dissolved in 20 mL anhydrous DMF, then K2CO3 (8 mmol) was added, and ethyl 4-bromobutanoate or ethyl 8-bromooctanoate(8 mmol) was dropped into the solution. Cut off from the air, the solution was stirred at room temperature for overnight,and then adjusted to pH 7-8 with HCl (1 mol/L), then extracted with 50 mL ×3 ethyl acetate and the organic phase was combined, and washed with brine, dried over MgSO4 and evaporated. The crude product was purified by chromatography on a silica gel column (EtOAc/petroleum ether, 1 : 1) to give desired compounds 6a-6p.

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

Reference:
Article; Xu, Zhaoxing; Yang, Yongchao; Mai, Xi; Liu, Bin; Xiong, Yuanzhen; Feng, Lihuang; Liao, Yijing; Zhang, Yu; Wang, Huanlu; Ouyang, Leiting; Liu, Shuhao; Chemical and Pharmaceutical Bulletin; vol. 66; 4; (2018); p. 439 – 451;,
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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. 85920-63-4, name is 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione, A new synthetic method of this compound is introduced below., COA of Formula: C8H10O5

General procedure: To a round bottomed flask equipped with a magnetic bar, benzaldehyde 2a (200 mg, 1.15 mmol) and freshly prepared benzoyl Meldrum?s acid 4a (430 mg, 1.73 mmol) were added in 2 mL THF-H2O (5:1). Then the catalyst DMEDA (25 mL, 0.23 mmol) was added and the reaction mixture was allowed to stir for 12 h at 55 C. After the complete consumption of benzaldehyde 2a (monitored by TLC), reaction mixture was filtered through anhydrous Na2SO4 and the residue was purified by column chromatography over silica gel using ethyl acetate in petroleum ether as eluent. The product 5a was obtained as pale yellow viscous oil in 82% yield (261 mg).

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; Khopade, Tushar M.; Warghude, Prakash K.; Mete, Trimbak B.; Bhat, Ramakrishna G.; Tetrahedron Letters; vol. 60; 2; (2019); p. 197 – 200;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 252881-74-6, A common heterocyclic compound, 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, molecular formula is C13H27NO5, 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.

A solution of 25 mg of 3-(3-(4-(piperidin-1-yl)-2-(4-(3-(trifluoromethyl)-benzylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)benzylthio)benzoic acid 8.1, 12 mg of tert-butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, and 17.8 mg of diisopropylethylamine in 1 mL of DMF was treated with 15 mg of HATU. The mixture was stirred for 1 h and then the product was isolated by reverse phase HPLC eluting with 0.05% TFA in a water/acetonitrile gradient.

The synthetic route of 252881-74-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ardelyx, Inc.; Lewis, Jason G.; Jacobs, Jeffrey W.; Reich, Nicholas; Leadbetter, Michael R.; Bell, Noah; Chang, Han-Ting; Chen, Tao; Navre, Marc; Charmot, Dominique; Carreras, Christopher; Labonte, Eric; (323 pag.)US9301951; (2016); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics