Author: Jessica.F

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. 18595-18-1, name is Methyl 3-amino-4-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 18595-18-1

Example 1 A Preparation of 4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(dimethylcarbamoyl)-1H- indazol-3-yl)cyclohex-3-enecarboxylic acid (1A) Step 1: Preparation of methyl 1H-indazole-6-carboxylate (A-2). Methyl 3-amino-4-methylbenzoate (A-l) (5.0 g, 30.2 mmol) was dissolved in AcOH (140 mL). Sodium nitrite (2.1 g, 30.2 mmol) in water (3.5 mL) was added drop-wise to the solution of starting material under ice-cooling at room temperature. The ice bath was removed and the mixture was stirred overnight. The half of the solvents were evaporated, the mixture was diluted with water (80 mL) and extracted with EtOAc(3×30 mL). The collected organic phase was washed with water and brine (2×200 mL), dried and evaporated to afford 2 (4.4 g), yield 83%. LCMS (ESI): calc’d for C9H8N202, [M+H]+: 177, found: 177.

The synthetic route of 18595-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth Jay; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard Thomas; ZHANG, Dongshan; WO2014/26328; (2014); 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. 82911-71-5, name is (9H-Fluoren-9-yl)methyl 1H-benzo[d][1,2,3]triazol-1-yl carbonate, A new synthetic method of this compound is introduced below., 82911-71-5

4-[Bis(tert-butyl)phosphonomethyl]-N-Fmoc-DL-phenylalanine (Compound No. 4) A solution of amine compound No. 3 (770 mg, 1.93 mmol) in dioxane (10 mL) is stirred at room temperature 20 min) with aqueous 1 N NaOH (10 mL, 10 mmol, 5 equiv.). Carbon dioxide is then bubbled in (resulting pH 8.0-8.5) and Fmoc-OBT (857 mg. 2.40 mmol, 1.2 equiv) is added as a suspension in dioxane (3*10 mL) and stirred overnight at ambient temperature. The reaction mixture is partitioned between cold aqueous 5% citric acid (200 mL) and CHCl3 (3*100 mL); the combined organic is washed with cold 5% citric acid (1*100 mL); brine (1*200 mL); dried (MgSO4) and taken to dryness, yielding a light yellow resin (1.92g). The resin is taken up in CHCl3 and filtered through a silica pad. Unreacted Fmoc-OBT and faster impurities are removed with CHCl3 (5*100 mL) with product then being eluted (8*100 mL) with 1% EtOH in CHCl3 and taken to dryness, providing a foam (953 mg) which is dissolved in Et2 O (5 mL) and cooled with petroleum ether (20 mL) to yield compound No. 4 as a white powder: 835 mg (73%); mp 65-70 C. (gas, dec.).

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; The United States of America as represented by the Secretary of the Department of Health and Human Services; US5264607; (1993); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, 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 25597-16-4, 25597-16-4

The resulting product (0.50, 2.6mmol) from step 5, ethyl 4,4,4-trifluorocrotonate (1.7g, 10.1mmol) and anhydrous potassium carbonate (0.36g, 5.6mmol) were dissolved in DMF (20mL), and then the system was stirred for 2hrs at 90C. At the end of reaction, the reaction system was cooled to room temperature and added with water, the mixture was extracted with ethyl acetate, and the organic phase was dried and evaporated in vacuum to obtain 0.50g of the product (50%) by column chromatography. 1HNMR (400 MHz, d-CDCl3), delta 7.65(s, 1H), 7.16 (s, 1H), 7.07(s, 1H), 5.73(m, 1H), 4.30(m, 2H),1.27(m,3H)

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, Ethyl 4,4,4-trifluorocrotonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangzhou Institute Of Biomedicine And Health, Chinese Academy Of Sciences; ZHANG, Yanmei; TALLEY, John Jeffrey; OBUKOWICZ, Mark G.; TU, Zhengchao; TORTORELLA, Micky; WANG, Yican; LIU, Jianqi; CHEN, Yan; LIU, Xiaorong; LU, Xin; EP2845854; (2015); A1;,
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40800-65-5, A common compound: 40800-65-5, name is Ethyl 4-amino-3-methylbenzoate, 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 ethyl 4-amino-3-methylbenzoate (7.43 g)in DMF ..(35 ml) were added DMAP (506 mg) and acetic anhydride(4.66 g) at ambient temperature. After stirring for 4 hours,the reaction mixture was diluted with water (40 ml) andextracted with EtOAc (4 x 60 ml). The combined organicextracts were washed with saturated NaHCOs (2 x 30 ml) andbrine (3 x 100 ml) . The organic layer was dried over MgSC>4 andfiltered. Evaporation gave a residue which was triturated withEtOAc – n-hexane to give ethyl 4-(acetylamino)-3-methylbenzoate(4.324 g) as white crystals. The filtrate was evaporated andtriturated with EtOAc – n-hexane to give second crop (1.64 g).NMR(DMSO-d6,8) :. 1.31 (3H, t, J = 7.1Hz), 2.11 (3H, s) , 2.28(3H, s), 4.29 (2H, q, J = 7.1 Hz), 7.7-7.8 (3H, m), 9.37 (1H,br s) .MS: 244 (M+Na). .

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, Ethyl 4-amino-3-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; DAICEL CHEMICAL INDUSTRIES, LTD.; WO2004/108686; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common heterocyclic compound, 140-39-6, name is p-Tolyl Acetate, molecular formula is C9H10O2, 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. 140-39-6.

NBS (13.91 g, 0.12 mol, 0.9 eq) and AIBN (2.17 g, 0.01 mol,0.1 eq) were placed in a Schlenk flask and put under an argonatmosphere. CHCI3was added followed by p-toy acetate (19.67 g, 0.13 mol). The mixture was refluxed for 4 h. After cooling down the volume of the mixture was reduced on rotavap to approximately a third and the suspension was filtered. 200 mL of CHCI3was added to the filtrate and it was 3x washed with 80 mL of water, the combined organic layers were dried with MgSC>4, filtered and volatiles were removed on rotavap. 5 mL of AcOEt was added, the mixture was shortly sonicated and while stirring, 40 mL of hexane was added causing precipitation. The mixture was put to a freezer overnight and then filtered washing the white solid with 25 mL of hexane giving 12.05 g (41 %, 0.05 mol) of the product. It was stored in the freezer. The NMR spectrum was in accordance with the literature (J. Org. Chem. 1981, 46 (15), 3029-3035)

The synthetic route of p-Tolyl Acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE JOHNS HOPKINS UNIVERSITY; INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY AS CR V.V.I.; SLUSHER, Barbara; RAIS, Rana; VAVRA, Jan; TICHY, Toma?; MAJER, Pavel; JANCARIK, Andrej; TENORA, Luka?; (148 pag.)WO2018/94334; (2018); A1;,
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2555-28-4, A common heterocyclic compound, 2555-28-4, name is 7-Methoxy-4-methylcoumarin, molecular formula is C11H10O3, 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 mixture of compound 22b (1.0 g, 5.3 mmol), NBS (1.4 g, 7.9 mmol) and BPO (20 mg) in CHCl3(30 mL) was heated to reflux at 70C for 8 hours. The reaction mixture was cooled to 0C, diluted with water, and extracted with CHCl3. The organic phase was concentrated in vacuo to afford compound 22c (1.0 g, 71 %).

The synthetic route of 2555-28-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KOZLOWSKI, Joseph; COBURN, Craig; YU, Wensheng; TONG, Ling; HU, Bin; ZHONG, Bin; HAO, Jinglai; WANG, Dahai; JI, Tao; WO2015/89810; (2015); A1;,
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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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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

1559-02-0, 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 1559-02-0 as follows.

To a solution of diethyl cyclopropane-1,1-dicarboxylate (4.77 g, 25.6 mmol) in ethanol (40 mL) was added KOH (1.43 g, 25.6 mmol) in H2O (8 mL), and the reaction mixture was stirred at room temperature overnight. The ethanol was removed under reduced pressure. The residue was neutralized with HCl (6 mL, 5 mol/L), then extracted with EtOAc (100 mL*3). The combined organic phases were dried over Na2SO4, filtered and the filtrate was concentrated in vacuo to give the title compound as a white solid (3.58 g, 88.4 %). 1H NMR (400MHz, CDCl3): delta 1.27 (t, J=6.7Hz, 3H), 1.83 (m, 2H), 1.86 (m, 2H), 4.25 (m, 2H).

According to the analysis of related databases, 1559-02-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; Xi, Ning; XI, Ning; (152 pag.)EP2408300; (2016); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

35180-01-9,Some common heterocyclic compound, 35180-01-9, name is Chloromethyl isopropyl carbonate, molecular formula is C5H9ClO3, 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 stirred suspension of PMPA (7.26 g, 0.026 mmol) in DMF (100 mL) was added Et 3 N (10.8 mL, 0.0778 mmol) at 50 C. The reaction mixture became homogeneous and chloromethyl isopropyl carbonate (12.1 g, 0.0778 mmol) was added to the reaction mixture and stirring was continued at 50 C. (oil bath temperature) for 20 h. The solvent was removed under reduced pressure and the crude product was chromatographed on a silica gel column. Elution with 10% isopropanol in CH 2 Cl 2 removed all nonpolar impurities. Further elution with the same solvent mixture yielded 1.3 g (about 10%) of the prodrug.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 35180-01-9, its application will become more common.

Reference:
Patent; GILEAD SCIENCES INCORPORATED; ARIMILLI, MURTY N; CUNDY, KENNETH C; DOUGHERTY, JOSEPH P; KIM, CHOUNG U; OLIYAI, REZA; STELLA, VALENTINO J; (59 pag.)JP2015/164934; (2015); A;,
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Ester – an overview | ScienceDirect Topics