Esters-buliding-blocks

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. 58677-05-7, name is Ethyl 2-amino-5-methylbenzoate, A new synthetic method of this compound is introduced below., name: Ethyl 2-amino-5-methylbenzoate

a) 5-Methyl-2-methylaminobenzyl chloride hydrochloride Ethyl 2-amino-5-methylbenzoate was treated with dimethylsulfuric acid to give a N-methylated product. The N-methylated product was reduced using lithium aluminum hydride to give 5-methyl-2-methylaminobenzyl alcohol.

The synthetic route of 58677-05-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nippon Chemiphar Co., Ltd.; US5082943; (1992); A;,
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Synthetic Route of 457097-93-7, These common heterocyclic compound, 457097-93-7, name is Methyl 4-amino-3-(trifluoromethoxy)benzoate, 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.

(b) 4-Amino-3-chloro-5-trifluoromethoxy-benzoic acidmethyl ester The product of the previous step (200.0 mg, 0.74 mmol) was dissolved in a mixture of ACN (9.44 mL) and DMA (0.944 mL) at RT. To this stirred solution was added N-chlorosuccinimide (108.2 mg, 0.81 mmol). The resulting mixture was heated at 60 C. for 1 h, cooled to RT and partitioned between EtOAc (20 mL) and saturated sodium bicarbonate (4 mL). The organic layer was washed with saturated sodium bicarbonate (4 mL) and brine (4 mL), dried over sodium sulfate, filtered, and concentrated to give a yellowish oil, which was purified by silica gel chromatography (12 g silica gel, 0-40% EtOAc/hexanes) to give the title intermediate as a white solid (173.8 mg, 88% yield). Structure confirmed by NMR.

The synthetic route of 457097-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LONG, Daniel D.; MCKINNELL, Robert Murray; JIANG, Lan; LOO, Mandy; LEPACK, Kassandra; VAN ORDEN, Lori Jean; OGAWA, Gavin; HUANG, Xiaojun; ZHANG, Weijiang; US2013/115194; (2013); A1;,
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Reference of 454-31-9,Some common heterocyclic compound, 454-31-9, name is Ethyl 2,2-difluoroacetate, molecular formula is C4H6F2O2, 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.

Into an 100-mL 3 -necked round-bottom flask was added a solution of 1 ,4- dibromobenzene (0.23 g, 0.99 mmol) in tetrahydrofuran (50 mL). The solution was placed under nitrogen and cooled to -78C. w-Butyllithium (0.4 mL,2.5 M) was added dropwise, and the resulting solution was stirred for 30 min at the same temperature. Ethyl 2,2-difluoroacetate(0.14 g, 1.1 mmol) was added dropwise to the mixture and the resulting solution was stirred for an additional 1 h at -78C. The reaction was quenched by the careful addition of hydrochloric acid (2.0 mL, 1.0 M). The mixture was extracted with ethyl acetate (2 x 10 mL), and the organic layers were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo to afford l-(4-bromophenyl) 2,2-difluoroethan-l-one. GCMS calc’d for C8H5BrF20[M]+: 234, found 234.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew Lloyd; DINSMORE, Christopher; FULLER, Peter; GUERIN, David; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; ZHANG, Hongjun; FALCONE, Danielle; TORRES, Luis; BRUBAKER, Jason; ZENG, Hongbo; CAI, Jiaqiang; DU, Xiaoxing; WANG, Chonggang; BAI, Yunfeng; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146490; (2014); A1;,
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Related Products of 50893-36-2, These common heterocyclic compound, 50893-36-2, name is 1-Chloroethyl ethyl carbonate, 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.

EXAMPLE 10 To a mixture of 1-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1H-tetrazol-1-yl)phenyl]-2-imidazolidinone (0.61 g) and 1-chloroethyl ethyl carbonate (3.7 g) was added acetonitrile (1 ml), and the mixture was stirred for 38 hours at 95¡ã C. The reaction mixture was concentrated under reduced pressure. To the residue was added diisopropyl ether (10 ml), and the resulting powder was collected by filtration. The powder was subjected to ODS column chromatography (eluent: methanol/water=3/2). The elude was concentrated in vacuo. The residue was dissolved in water (10 ml), and lyophilized to give 1-[(2R,3R)-2-(2,4-difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-(1H-tetrazol-1-yl)phenyl]-1-imidazolidinyl]butyl]-4-[1-(ethoxy-carbonyloxy)ethyl]-1H-1,2,4-triazolium chloride (Compound 7,90 mg) as a white powder. 1H-NMR(d6-DSMO) delta: 0.97(3H,d,J=7 Hz), 1.21,1.22(3H,t,J=7 Hz), 1.79,1.80(3H, d,J=6 Hz), 3.62~4.23(6H,m), 4.65~5.10(3H,m), 6.69~6.82(2H,m), 6.94~7.04(1H,m), 7.26~7.38(2H,m), 7.90(4H,s), 9.23(0.5H,s), 9.27(0.5H,s), 10.08(1H,s), 10.72(0.5H,s), 10.82(0.5H,s).

The synthetic route of 50893-36-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6407129; (2002); B1;,
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Adding a certain compound to certain chemical reactions, such as: 57381-62-1, name is Methyl 2-bromo-4-chlorobenzoate, 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 57381-62-1, name: Methyl 2-bromo-4-chlorobenzoate

In a 500 ml round-bottomed flask, 30 g (68.9 mmol) of the compound of formula C-1,17 g (68.2 mmol) of methyl 2-bromo-4-chlorobenzoate,1.6 g (1.38 mmol) of tetrakistriphenylphosphine palladium was added to 150 ml of tetrahydrofuran, mixed with 80 ml of an aqueous solution of 28.6 g (207 mmol) of potassium carbonate and refluxed for 24 hours. The impurities were removed using chloroform and water, and then anhydrous magnesium sulfate was added to remove moisture. The solution was filtered and then recrystallized using chloroform and ethanol to obtain 21.2 g (yield 65percent) of the formula C-2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-bromo-4-chlorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; LG Chemical Co.,Ltd; Kim, Su Yeon; Lee, Ho Yong; Jo, Sung Mi; (43 pag.)KR2016/2354; (2016); A;,
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Synthetic Route of 37746-78-4,Some common heterocyclic compound, 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, molecular formula is C6H9BrO2, 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 6 N NaOH (0.1 mL) solution was added dropwise into a solution of 13 (100 mg, 0.38 mmol) and 30% H2O2 (0.05 mL) in EtOH (5 mL) at 0 C. The reaction mixture which resulted, was stirred for 2 h at the same temperature after which water was added to the reaction mixture and it was extracted with CH2Cl2 (2 * 10 mL). The combined organic extracts were washed with brine (2 * 15 mL). The organic layer was dried (MgSO4) and concentrated under vacuum to yield the crude epoxide ethyl ester. The crude compound was purified by flash column chromatography (10% EtOAc in hexanes) on silica gel to afford epoxide ethyl ester 29 (55 mg, 52%). 1H NMR (300 MHz, CDCl3): delta 7.99 (d, J = 8.4 Hz, 2H), 7.55 (d, J = 8.4 Hz, 2H), 4.46 (d, J = 1.8 Hz, 1H), 4.32 (m, 2H), 3.70 (d, J = 1.8 Hz, 1H), 1.38 (m, 12H); 13C NMR (75 MHz, CDCl3): delta 191.3, 167.31, 158.5, 132.5, 128.6, 126.0, 62.3, 55.2, 53.0, 35.3, 31.0, 14.1. HRMS (ESI) (M+Na)+, calcd for C16H20O4Na 299.1259; found 299.1248.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (E)-Ethyl 4-bromobut-2-enoate, its application will become more common.

Reference:
Article; Tiruveedhula, V.V.N. Phani Babu; Witzigmann, Christopher M.; Verma, Ranjit; Kabir, M. Shahjahan; Rott, Marc; Schwan, William R.; Medina-Bielski, Sara; Lane, Michelle; Close, William; Polanowski, Rebecca L.; Sherman, David; Monte, Aaron; Deschamps, Jeffrey R.; Cook, James M.; Bioorganic and Medicinal Chemistry; vol. 21; 24; (2013); p. 7830 – 7840;,
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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, Quality Control of Ethyl 4,4,4-trifluorocrotonate

General procedure: To a solution of trifluorocrotonic acid (1.0 equiv) in DMF, was added the amino acid methyl ester hydrochloride (1.2 equiv), DIPEA (4.0 equiv), HBTU (1.2 equiv) and HOBt (1.2 equiv) in this order. The mixture was stirred overnight at room temperature under argon atmosphere. The solvent was evaporated under vacuum and the residue dissolved in ethyl acetate. The organic layer was washed with 10% citric acid aqueous solution (two times), water, 10% K2CO3aqueous solution (two times) and brine, dried over Na2SO4, filtrated and evaporated. The crude product was purified by column chromatography (EtOAc/cyclohexane: 3/7) to afford the corresponding alkene.

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

Reference:
Article; Schweitzer-Chaput, Bertrand; Keita, Massaba; Milcent, Thierry; Ongeri, Sandrine; Crousse, Benoit; Tetrahedron; vol. 68; 35; (2012); p. 7028 – 7034;,
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Some common heterocyclic compound, 14273-90-6, name is Methyl 6-bromohexanoate, molecular formula is C7H13BrO2, 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. HPLC of Formula: C7H13BrO2

3,5-Dimethyl-4-(3-phenyl-1H-indol-5)-isoxazole (0.5 g, 1.75 mmol) was weighed and dissolved in 30 ml of acetonitrile.Cesium carbonate (2.5 g, 5 mmol) was added, and then methyl 6-bromohexanoate (0.41 g, 2.0 mmol) was added dropwise thereto, and the mixture was reacted at 70 ¡ã C for 2 h.After completion of the reaction, ethyl acetate was extracted (40 ml ¡Á 3), and the organic phase was combined and washed with a saturated sodium chloride solution.Dry over anhydrous sodium sulfate overnight. After filtration, the solvent was evaporated under reduced pressure and purified by column chromatography.A white solid was obtained in an amount of 0.38 g, yield 84percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 14273-90-6, its application will become more common.

Reference:
Patent; Shenyang Pharmaceutical University; Liu Dan; Zhao Linxiang; Yang Jinyu; Cheng Gaoliang; Bao Yu; Jing Yongkui; (20 pag.)CN109096272; (2018); A;,
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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 618-89-3 as follows. Formula: C8H7BrO2

To a soiuiion of Compound 5-1 (2,00 g, 9.30 mmol, 1.00 eq) and morpholine (972 mg, 1 1.2 mmol, 1.20 eq) in toluene (20 n L) was added Cs2Ci (6.10 g, 1 8.6 mmol 2.00 eq), BINAP (289 mg, 465 umol, 0,05 eq) and Pd(OAe)2 (104 mg, 465 umo, 0.05 eq). The mixture stirred at 100 C in N2 atmosphere for 1 8 hr. The solid was filtered off and the filtrate was concentrated in vacuum. The residue was purified by column chromatography (PE:EtOAc=10: 1 to 5: 1 ) to afford Compound 6-2 (1.40 g, 69% yield) as a colorless oil. ‘HNMR: (400 MHz, CDCb) delta 7.607 (s, 3H), 7.567 (d, J=8 Hz, IH), 7.357 ( =4 Hz, I H), 7.134-7.128 (m, 4H), 3.930 (s, 3H), 3.897 (t, J-4.8 Hz, 4H), 3.230 (t, J=4.8 Hz, 4H).

According to the analysis of related databases, 618-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF UTAH RESEARCH FOUNDATION; VANKAYALAPATI, Hariprasad; SHARMA, Sunil; LIU, Xiaohui; COBURN, Craig; (106 pag.)WO2017/4519; (2017); A1;,
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Application of 5616-81-9, A common heterocyclic compound, 5616-81-9, name is tert-Butyl 2-(methylamino)acetate, molecular formula is C7H15NO2, 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.

Sarcosine tert-butylester (0.7 ml, 4.50 mmol) was added to perchlorate 3b(0.1 g, 0.27 mmol), and the mixture heated under reflux for 30 min. The color of the mixture turns from yellow to cherryred,then turns brown. The mixture was cooled, poured into2 (20 ml), and the formed emulsion extracted withEtOAc (2¡Á10 ml). The organic extract was evaporated, theresidue extracted several times with petroleum ether, andthe extract evaporated. The obtained tert-butyl (2-{(methyl)-[6-cyano-7-methyl-2-(4-methylphenyl)indolizin-5-yl]-amino})acetate (2c) was recrystallized from EtOH. Yield 20 mg (20%), yellow crystals.

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; Babaev, Eugene V.; Nevskaya, Aleksandra A.; Dlynnikh, Ilya V.; Chemistry of Heterocyclic Compounds; vol. 51; 3; (2015); p. 269 – 274; Khim. Geterotsikl. Soedin.; vol. 51; 3; (2015); p. 269 – 274,6;,
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