Category: esters-buliding-blocks

Application of 555-43-1,Some common heterocyclic compound, 555-43-1, name is Propane-1,2,3-triyl tristearate, molecular formula is C57H110O6, 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.

Alcoholysis of triglycerides Alcoholysis of pure triglycerides (TGs), including trilaurin, tripalmitin and tristearin, was carried out. Most diglyceride (DG) obtained from alcoholysis reaction were 1,2-DG. A high amount OF uNREACTED TG remained in the reaction mixture. Acyl migration was observed during the reaction, especially in hydrolysis reaction, as illustrated in Figure 18. Figure 18 shows data from alcoholysis reaction showing the 1,3- DS/1, 2-DS ratio during alcoholysis and hydrolysis of tristearin. DEP = D-EP100, RM = Lipozyme RM IM, Hx = n-hexane, HYD = hydrolysis, ALC = alcoholysis. The reaction catalyzed by Lipozyme RM IMTM, though gave lower yield, showed higher acyl migration than the reaction catalyzed by D-EP100. Low acyl migration was observed in alcoholysis using CAL-B after 6h. This could be because 1,2- DG and 1,3-DG were produced at the same time according to the non-specificity of CAL- B. D-EP 100 showed higher activity than CAL-B and Lipozyme RM, respectively, in alcoholysis of tripalmitin and tristearin. Effect OF AW : HIGHER yield and less MG was obtained from alcoholysis at aW 0.11 than 0.43. It was found that MG was increased with increasing aw. Effect of solvents (on yield and acyl migration): Highest yield was obtained with MTBE. Alcoholysis in n-hexane and isooctane gave moderate yield, while acetone was a poor solvent for Lipozyme RM. The reaction performed in n- hexane showed faster acyl migration than in MTBE, as illustrated in Figures 18 and 19. Figure 19 illustrates data from the hydrolysis of trilaurin at 60C by Lipozyme RM IM (DG = dilaurin).

The synthetic route of 555-43-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DIVERSA CORPORATION; WO2005/32496; (2005); A2;,
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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. 5048-82-8, name is Ethyl 3-(4-aminophenyl)acrylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C11H13NO2

PREPARATION 44 To a mixture of ethyl 4-aminocinnamate (300 mg), triethylamine (167 mg) and dichloromethane (3 ml) was added a solution of propionyl chloride (182 mg) in dichloromethane (1 ml) in an ice-water bath, and the mixture was stirred for 1 hour at the same temperature. To the reaction mixture was added 4 drops of N,N-dimethylpropanediamine, and the mixture was further stirred for 5 minutes. The reaction mixture was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The residue was crystallized from diisopropyl ether to give ethyl 4-propionamidocinnamate (341 mg) as a colorless powder. mp: 138¡ã C. NMR (CDCl3, delta): 1.26 (3H, t, J=8 Hz), 1.34 (3H, t, J=8 Hz), 2.42 (2H, q, J=8 Hz), 4.26 (2H, q, J=8 Hz), 6.37 (1H, d, J=16 Hz), 7.21 (1H, br s), 7.49 (2H, d, J=8 Hz), 7.58 (2H, d, J=8 Hz), 7.68 (1H, d, J=16 Hz)

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; Fujisawa Pharmaceutical Co., Ltd; US5574042; (1996); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 6279-86-3,Some common heterocyclic compound, 6279-86-3, name is Triethyl methanetricarboxylate, molecular formula is C10H16O6, 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.

Indoline (9a) (1.6 mL, 12.9 mmol) was added dropwise with stirring to triethyl methanetricarboxylate (3.2 mL, 12.9mmol) heated to 215C, at such a rate that the temperature of the reaction mixture was maintained within ¡À5C of the initial temperature. The ethanol eliminated during the reaction was distilled through a suitable still-head. After adding all the indoline the reaction mixture was maintained at the same temperature for 10-15 min, after which it was cooled. The solid ester 5a was filtered off, washed with water, and dried. Yield 1.3 g (38%); mp 303.0 -304C LC-MS (M+1) 260.4 1H NMR (300 MHz, DMSO) delta 13.10 (s, 1H), 7.68 (d, J = 8.2 Hz, 1H), 7.52 (d, J = 7.1 Hz, 1H), 7.22 – 7.13 (m, 1H), 4.33 (q, J = 7.1 Hz, 2H), 4.26 – 4.16 (m, 2H), 3.37 (s, 1H), 3.32 (s, 1H), 1.31 (t, J = 7.1 Hz, 3H).

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

Reference:
Article; Huddar, Srigouri; Jang, Soojin; Kim, Hyung Jun; Lee, Sunkyung; Park, Chul Min; Bioorganic and medicinal chemistry letters; (2020);,
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Application of 40872-87-5,Some common heterocyclic compound, 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, molecular formula is C8H8ClNO2, 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 methyl 3-amino-4-chlorobenzoate (3.00 g, 16.2 mmol) and l-(morpholin-4- yl)cyclopropanecarboxylic acid hydrochloride (1:1) (example 65A, 6.71 g, 32.3 mmol, 2 equiv) in DMF (50 mL) was added (benzotriazol-l-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PYBOP, 16.8 g, 32.3 mmol, 2 equiv) and diisopropylethylamine (14.1 mL, 80.8 mmol, 5 equiv). The resulting mixture was stirred at room temperature for 3 days. (Benzotriazol-1- yloxy)tripyrrolidinophosphonium hexafluorophosphate (PYBOP, 16.8 g, 32.3 mmol, 2 equiv) and diisopropylethylamine (14.1 mL, 80.8 mmol, 5 equiv) were added and the resulting mixture was stirred at 60 C over night. The mixture was concentrated under reduced pressure, was then dissolved in dichloromethane, was washed with IN aqueous hydrogen chloride solution and saturated, aqueous sodium bicarbonate solution, was dried over sodium sulfate and concentrated under reduced pressure. The remaining solids were then triturated with ethanol (40 mL), and the resulting mixture was stirred for 30 minutes. The remaining solids were removed by filtration, washed with ethanol, and were dried at 50 C under reduced pressure. The remaining solids were then triturated with ethanol (70 mL), and the resulting mixture was stirred under reflux. After cooling to room temperature, the remaining solids were removed by filtration, washed with ethanol, and were dried at 50 C under reduced pressure to give the title compound (3.60 g). LC-MS (Method 4): Rt= 1.23 min; MS (ESIpos): m/z = 339 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-amino-4-chlorobenzoate, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; THEDE, Kai; SCOTT, William Johnston; BENDER, Eckhard; GOLZ, Stefan; HAeGEBARTH, Andrea; LIENAU, Philip; PUEHLER, Florian; BASTING, Daniel; SCHNEIDER, Dirk; MOeWES, Manfred; WO2014/147182; (2014); A2;,
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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. 178312-47-5, name is Ethyl 4,4-difluorocyclohexanecarboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H14F2O2

Under nitrogen atmosphere, 2.3 g of ethyl 4,4- difluorocyclohexanecarboxylate was dissolved in 50 ml of tetrahydrofuran. Thereto 0.46 g of lithium aluminum hydride was added at 0C and the mixture was stirred at 0C for an hour. Thereafter, 1N aqueous sodium hydroxide was added to the reaction mixture, and formed solids were filtered and then washed with ethyl acetate. The filtrate and the washing solution were combined, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain (4, 4-difluorocyclohexyl) methanol.

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; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2005/63694; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 107045-28-3,Some common heterocyclic compound, 107045-28-3, name is tert-Butyl 4-(aminomethyl)benzoate, molecular formula is C12H17NO2, 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 5-bromo-2-iodobenzoic acid (5. 00g, 15. [3MMOL)] in dimethylformamide [(60ML)] was treated with EDAC. [HC1] (3.. [51G, 18. 4MMOL), 1-] [HYDROXYBENZOTRIAZOLE] hydrate (2. [48G,] 18. 4mmol), and 4-aminomethylbenzoic acid tert-butyl ester (3.74g, 18. [4MMOL),] then stirred overnight at room temperature. The solution was treated with water [(40ML),] saturated aqueous sodium bicarbonate solution (15mL), followed by water [(40ML)] and the mixture stirred at room temperature for 1 hour. The solid was collected by filtration, washed with water and allowed to air dry overnight. The solid was heated in hexanes/ethyl acetate 2: 1, cooled to room temperature, and the crystals collected by filtration. Drying afforded the product as 6.30g of white solid (79.8% yield). [1H-NMR] [(CDC13)] ; d 7.98-7. 96 (d, [2H),] 7.70-7. 68 (d, 1H), 7.53-7. 52 (d, [1H),] 7.44-7. 43 (d, [2H),] 7.24-7. 21 (dd, 1H), 6.13 (bs, 1H), 4.67 (d, 2H), 1.60 (s, [9H).] MS: M+ +1 = 515.9/517. 9 Da.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 4-(aminomethyl)benzoate, its application will become more common.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/14379; (2004); A1;,
Ester – Wikipedia,
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. 1105187-36-7, name is Methyl 3-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 3-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylate

Methyl 3-bromo-6-iodo-4H-thieno[3,2-b]pyrrole-5-carboxylate (173 mg, 0.45 mmol), 3-acetamido-phenylboronic acid (80 mg, 0.45 mmol), tetrakis triphenylphosphine palladium (0) (26 mg, 0.02 mmol) and potassium carbonate (0.45 ml, 2M aq. solution, 0.90 mmol) were mixed under nitrogen atmosphere in degassed 1,2-dimethoxyethane (4 mL). The reaction mixture was refluxed overnight. Water (10 mL) was added and the mixture was extracted with ethyl acetate (2×15 mL). After drying with MgSO4, filtering and evaporation of the solvent, the product was purified by silica gel flash chromatography (40% ethyl acetate in iso-hexane) to give the desired product (62 mg, 32% yield). ESI-MS [M+H] 395, 393; 1H NMR (400 MHz, ODd3) O 9.05 (br 5, 1 H), 7.75 (m, 1 H), 7.48 (dm, J = 7.7 Hz, 1 H), 7.39 – 7.29 (m, 2H), 7.20 (brs, 1H), 7.14 (brs, 1H), 3.80 (5, 3H), 2.13 (5, 3H).

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 1105187-36-7.

Reference:
Patent; OXFORD UNIVERSITY INNOVATION LIMITED; GISING, Johan; LINDSTROM, Stefan; ANTONOV, Dmitry; BRANDT, Peter; BELFRAGE, Anna Karin; BREM, Juergen; SCHOFIELD, Christopher J.; (161 pag.)WO2018/215800; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 32122-09-1, name is Ethyl 2-(benzyloxy)acetate, A new synthetic method of this compound is introduced below., Formula: C11H14O3

To the argonated flask filled with 750 ml of dry THF cooled to -78C, 200 ml (0.5 mol) of 2.5 M n-BuLi hexane solution were added, and then 28 ml (0.533 mol) of acetonitrile were added dropwise. The whole mixture was stirred at -78C for 2 h. To the suspension 77.7 g (0.4 mol) of ethyl 2-benzyloxyacetate obtained above were added dropwise and stirring was continued at -78C for 1 h. The reaction was quenched by adding saturated ammonium chloride solution. The mixture was poured onto ice-water and acidified with 6 M hydrochloric acid. Aqueous phase was extracted with diethyl ether. Combined organic phases were washed with brine and dried over anhydrous magnesium sulphate. Drying agent was filtered off and the solvent was evaporated under reduced pressure. Intermediate XII-1 was used in the next step without purification. MS-ESI: (m/z) calculated for C11H11NO2 [M+H]+: 190.22; determined 190.1.

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; CELON PHARMA S.A.; DYMEK, Barbara; ZAGOZDA, Marcin; WIECZOREK, Maciej; DUBIEL, Krzysztof; STANCZAK, Aleksandra; ZDZALIK, Daria; GUNERKA, Pawel; SEKULAR, Mariola; DZIACHAN, Maciej; (70 pag.)WO2016/157091; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 51498-33-0, 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 51498-33-0 as follows.

A mixture of 2-Chlorobenzimidazole (I) (0.9 g, 5.9 mmol) and ethyl-4-amino-cyclohexane carboxylate (1.1 g, 5.4 mmol) were placed in a glass high pressure tube. Diisopropylethylamine (2.8 mL, 16.2 mmol) was added, the reaction vessel was sealed and heated to 200 C. for 4 h and allowed to cool to room temperature. Next was added 5 mL EtOH and heated to dissolve the reaction mixture. The reaction mixture was partitioned between aqueous NaHCO3 and EtOAc, and the organic layer was washed with water and brine, dried over MgSO4, filtered and concentrated. Purification of the crude product on silica gel (gradient, 1:1 hexanes:EtOAc to EtOAc) gave the cis 4-(1H-benzimidazol-2-ylamino)-cyclohexanecarboxylic acid ethyl ester (J) (0.5 g) and the trans 4-(1H-benzimidazol-2-ylamino)-cyclohexanecarboxylic acid ethyl ester (K) (0.5 g). Data for (J): 1H NMR (300 MHz, CDCl3) delta7.28 (br s, 2 H), 7.02 (m, 2 H), 5.16 (br s, 1 H), 4.15 (q, 2 H), 3.97 (br s, 1 H), 2.40 (br s, 1 H), 1.80-1.54 (m, 8 H), 1.22 (t, 3 H); mass spectrum m/z 288 [(M+H)+; calcd for C16H22N3O2: 288].

According to the analysis of related databases, 51498-33-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Thompson, Wayne I.; Claremon, David A.; Munson, Peter M.; McCauley, John A.; US2002/55519; (2002); A1;; ; Patent; Merck & Co., Inc.; US6495561; (2002); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 58677-05-7, name is Ethyl 2-amino-5-methylbenzoate, 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. Product Details of 58677-05-7

Example 51; 2-(6-(3-Methoxyphenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoic acidIn a schlenck tube, a mixture of Intermediate 33 (2.55 mmol, 0.71 g), Intermediate 55 (2.57 mmol, 0.46 g), BINAP (0.25 mmol, 0.158 g), Pd2(dba)3 (0.13 mmol, 0.116 g) and NaO1Bu (6.35 mmol, 0.610 g) in toluene (20 ml) was heated at 11O0C for 12 hours, under argon atmosphere. The solvent was evaporated, the solid residue was suspended in water, the pH was taken to 6.5 and extracted with CHCI3. The crude mixture was purified by flash chromatography over SiO2 eluting with mixtures of hexane/ethyl acetate affording 0.580 g (yield 65%) of the expected compound. delta 1H NMR (300 MHz, CDCI3): 2.28 (s, 3H)1 2.34 (s, 3H), 3.85 (s, 3H), 6.95 (d, 1 H), 7.08(s, 2H), 7.23 (d, 1 H), 7.36 (t, 1H), 7.58 (s, 1 H), 7.83 (s, 1 H), 8.51 (s, 1 H).ESI/MS (m/e, %): 349 [(M+1) 100].

The synthetic route of Ethyl 2-amino-5-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LABORATORIOS ALMIRALL, S.A.; WO2009/21696; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics