Month: March 2021

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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Related Products of 75567-84-9, 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. 75567-84-9, name is Methyl 3-(4-bromophenyl)propanoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In distinct reactors, 3-(bromophenyl)-propionic methyl esters 16, 17 (1.0 equiv) were dissolved in toluene (7 mL). Phenyl boronic acids 18-21 (2 equiv) in EtOH (3.5 mL) and Na2CO3 2 M (2 M, aq, 3.0 equiv) were then added to the corresponding reactors, and the resulting mixtures were deoxygenated with a stream of N2. After 10 min, Pd(PPh3)4 (0.005 equiv) was added and each mixture was stirred at reflux temperature for 5 h under N2, then cooled to room temperature and treated as follows. Each solution was poured into a mixture of H2O (5 mL) and Et2O (5 mL), and the two phases were separated. The aqueous layer was washed with Et2O (5 mL), and the organic phases were combined and washed with 1 M NaOH (5 mL), followed by brine (5 mL), then dried over Na2SO4 and evaporated. Purification of each crude product performed by flash chromatography on silica gel (petroleum ether/EtOAc = 8/2) yielded the corresponding biphenyl propanoic acid methyl esters 22a-e (Scheme 3).

The chemical industry reduces the impact on the environment during synthesis Methyl 3-(4-bromophenyl)propanoate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Chiriano, Gianpaolo; De Simone, Angela; Mancini, Francesca; Perez, Daniel I.; Cavalli, Andrea; Bolognesi, Maria Laura; Legname, Giuseppe; Martinez, Ana; Andrisano, Vincenza; Carloni, Paolo; Roberti, Marinella; European Journal of Medicinal Chemistry; vol. 48; (2012); p. 206 – 213;,
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Adding a certain compound to certain chemical reactions, such as: 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, 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 756525-95-8, Formula: C11H23NO4

Preparation of (9H-fluoren-9-yl)methyl 2-((1-(3-(4-((2-(2-(3-(tert-butoxy)-3- oxopropoxy)ethoxy)ethyl)amino)piperidin-1-yl)-3-oxopropyl)-1H-indol-2-yl)methyl)-1,2- dimethylhydrazine-1-carboxylate (Fmoc-HIPS-PAPip(PEG2(CO2t-Bu))NH) (Figure 62) To a dried scintillation vial containing a magnetic stir bar was added Fmoc-HIPS- piperidinone (355 mg, 0.63 mmol), H2N-PEG2-COOtBu (175 mg, 0.76 mmol), 4 A molecular sieves (activated powder, 100 mg), and 1,2-dichloroethane (2.5 mL). The mixture was stirred for 1 h at room temperature. To the reaction mixture was added sodium triacetoxyborohydride (314 mg, 1.48 mmol). The mixture was stirred for 18 hours at room temperature. The resulting mixture was partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was washed with saturated aqueous NaHCO3 (2 x 5 mL), and brine (1 x 5 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to yield the title compound as a yellow oil, which was carried forward without further characterization.

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; REDWOOD BIOSCIENCE, INC.; RABUKA, David; ALBERS, Aaron Edward; KUDIRKA, Romas Alvydas; GAROFALO, Albert W.; WO2015/81282; (2015); 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. 40061-54-9, name is Ethyl 2-(2-chlorophenyl)acetate, A new synthetic method of this compound is introduced below., COA of Formula: C10H11ClO2

General procedure: Ethyl-2-arylacetate (2 mmol), aq.formaldehyde (1 mmol), aq.ammonia / aliphatic / aromatic amines (2 mmol) and a catalytic amount of piperidine and pyridine in abs. ethanol (250 mL) were refluxed for 4 hour. The course of the reaction was monitored by TLC, and after the disappearance of the starting materials, excess of alcohol is removed in vacuo and the residue extracted with benzene and washed with dil.HCl and then with water and dried. The dried benzene extract was purified by passing through a column of SiO2. The residue obtained on evaporation of the solvent, on crystallization (aq. EtOH) gave pure 3, 5-diarylpiperidin-2, 6-diones in appreciable yields (70-90percent).

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; Babu, Mariappan; Pitchumani, Kasi; Ramesh, Penugonda; Bioorganic and Medicinal Chemistry Letters; vol. 22; 2; (2012); p. 1263 – 1266;,
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Ester – an overview | ScienceDirect Topics

Reference of 99548-55-7,Some common heterocyclic compound, 99548-55-7, name is Methyl 4-bromo-2-methylbenzoate, molecular formula is C9H9BrO2, 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.

i 4-Bromo-2-bromomethylbenzoic acid, methyl ester The subtitle compound was prepared from 4-bromo-2-methylbenzoic acid methyl ester (22.5 g) according to the method of example 2 step (i). Yield 26.45 g. Used directly in the next step.

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

Reference:
Patent; AstraZeneca U.K. Limited; US6162808; (2000); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, 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. Application In Synthesis of tert-Butyl 9-Amino-4,7-dioxanonanoate

SI-22 (270 mg, 1.03 mmol, 1.2 eq.), COMU (440 mg, 1.03 mmol, 1.2 eq.), and N- methylmorpholine (283 pL, 2.57 mmol, 3 eq.) were dissolved in 1.5 mL of DMF and stirred for 1 min. Amino-PEG2-t-butyl ester (200 mg, 0.86 mmol, 1 eq.) was added in 2.5 mL of DMF and the reaction was stirred at room temperature for 1 h. The reaction was diluted with ethyl acetate (lOmL) and the organic phase washed with water (3xl5mL) and brine (lxl5mL). The organic layer was separated, dried over anhydrous MgSCE, and concentrated. The residue was purified by flash chromatography (DCM/EtOAc; 1 : 1) to provide the title compound as a colorless oil (212 mg, 43%). NMR (500 MHz, Chloroform-7) d 7.01 (t, J= 5.7 Hz, 1H), 6.71 (dt, J= 8.7, 2.4 Hz, 1H), 6.68 (s, 1H), 4.43 (s, 2H), 3.74 – 3.69 (m, 2H), 3.67 (td, J= 6.4, 2.0 Hz, 2H), 3.55 (d, j= 2.3 Hz, 4H), 3.51 (ddd, j= 6.5, 3.4, 1.5 Hz, 2H), 2.65 (s, 2H), 2.48 – 2.40 (m, 4H), 2.18 (qd, J= 7.6, 2.1 Hz, 1H), 1.90 (td, j= 6.6, 1.8 Hz, 2H), 1.41 (d, 7= 1.5 Hz, 2H), 1.40 (d, 7= 2.3 Hz, 9H), 1.11 (td, 7= 7.8, 2.6 Hz, 3H). HRMS (ESI) [M+Na]+ for C25H38N207Na 501.2571, found 501.2580.

The synthetic route of tert-Butyl 9-Amino-4,7-dioxanonanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; ZHANG, Xiaoyu; CROWLEY, Vincent; CRAVATT, Benjamin; (121 pag.)WO2020/77278; (2020); A1;,
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