Tag: M.W=100-200

Related Products of 145576-28-9, 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. 145576-28-9, name is Ethyl 4-methylenecyclohexanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of ethyl 4-methylenecyclohexanecarboxylate (0.15 g, 0.892 mmol) in diglyme (3 mL) was added a solution of sodium 2-chloro-2,2- difluoroacetate (0.544 g, 3.57 mmol) in 5 ml of diglyme via syringe pump at 0.5 ml/h at 150 C. The reaction was cooled to rt, then diluted with DCM and washed with water, brine, dried over Na2SO4, filtered and concentrated. The residue was chargedto a 40 g silica gel cartridge which was eluted with a 20 mm gradient of 0-20% EtOAc in hexane to yield ethyl 1,1-difluorospiro[2.5]octane-6-carboxylate. ?H NMR (400 MHz, CDC13) ppm 4.09 – 4.19 (2 H, m), 2.29 -2.45 (1 H, m), 1.89 -2.03 (2 H, m), 1.55 – 1.72(5 H, m), 1.45 – 1.54(1 H, m), 1.31 – 1.39 (1 H, m), 1.21 – 1.30(3 H, m), 0.84 – 0.94 (1 H, m).

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-methylenecyclohexanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (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. 106-32-1, name is Ethyl octanoate, A new synthetic method of this compound is introduced below., Product Details of 106-32-1

General procedure: In a typical run, a 50 mL stainless steel autoclave equipped with a transducer for online pressure monitoring was charged under air of Pd-pol (10.6 mg, Pd: 0.5 mol%), the substrate (carboxylic acid or ester, 1.0 mmol), bromobenzene (0.1 mmol, 15.7 mg) and alcohol (5.0 mL). The autoclave was then purged three times with hydrogen, then pressurized with 2 bars H2, set on a magnetic stirrer and heated to 40 C. After the minimum time needed to reach reaction completion, the autoclave was let to reach room temperature, the hydrogen was vented and the autoclave opened. When necessary, 3.0 mL diethyl ether was added to the mixture at the end of reaction in order to dissolve organic reactants and products. The catalyst was recovered by centrifugation. The yields were assessed by GLC analysis of the organic solution by using biphenyl (50.0 mg) as internal standard.

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; Dell’Anna, Maria Michela; Capodiferro, Vito Filippo; Mali, Matilda; Mastrorilli, Piero; Journal of Organometallic Chemistry; vol. 818; (2016); p. 106 – 114;,
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Related Products of 15441-07-3, 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. 15441-07-3, name is Methyl 3-(chlorosulfonyl)propanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In a 100 mL round bottom flask, to a solution of methyl 3-(chlorosulfonyl)propanoate (187 mg, 1 mmol) and S-trans, trans-farnesyl-L-cysteine methyl ester (339 mg, 1 mmol) in THF (5 mL) was added N,N-diisopropyl-ethyl-amine (0.52 mL, 3 mmol) dropwise. The solution was stirred at 0 0C for 30 min and then room temperature overnight. The mixture was diluted with ethyl acetate (60 mL) and washed by 0.5 N HCl (10 mL x 1), H2O (10 mL x 1) and brine (10 mL x 1). The organic layer was dried over Na2SO4 and concentrated in vacuo. The resulting residue was dissolved in THF (3 rnL) and a solution Of LiOH-H2O (420 mg, 10 mmol) in H2O (2 mL) was added slowly at 0 0C. The reaction was left at room temperature overnight. The solution was then diluted with ethyl acetate and washed by 0.5 N HCl (10 mL x 1), H2O (10 mL x 2) and brine (15 mL x 1). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was then further purified by preparative HPLC (100 mg, 22%) to yield Compound N-80. 1H-NMR (500 MHz, CD3OD): delta 1.50 (s, 3H), 1.51 (s, 3H), 1.57 (s, 3H), 1.61 (s, 3H), 1.86-1.89 (m, 2H), 1.95-2.00 (m, 4H), 2.01-2.06 (m, 4H), 2.65 (dd, J = 8.0, 14.0 Hz, IH), 2.71-2.76 (m, 2H), 2.84 (dd, J = 5.0, 14.0 Hz, IH), 3.13 (dd, J = 7.5, 13.5 Hz, IH), 3.24-3.29 (m, IH), 4.05 (dd, J = 5.0, 8.0 Hz, IH), 4.98-5.03 (m, 2H), 5.09-5.14 (t, J = 8.0 Hz, IH). 13C-NMR (125 MHz, CD3OD): delta 16.15, 16.30, 17.80, 25.95, 27.38, 27.79, 29.56, 30.44, 34.80, 40.78, 40.89, 49.82, 57.51, 121.64, 125.16, 125.46, 132.12, 136.27, 140.62, 174.04, 174.15; ES-MS: mass calcd for Chemical Formula: C21H35NO6S2 461.64. Found (M+) m/z 462.2, (M+Na) m/z 484.2.

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 3-(chlorosulfonyl)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SIGNUM BIOSCIENCES, INC.; STOCK, Jeffry, B.; STOCK, Maxwell; RAPOLE, Keshava; LEE, Seung-yub; VORONKOV, Michael; PEREZ, Eduardo; CHEN, Shuyi; CHEN, Jinglong; GORDON, Joel; WO2010/56778; (2010); A1;,
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1459-93-4, name is Dimethyl isophthalate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C10H10O4

Add 100 mL of tetrahydrofuran to the reaction flask.Then add 20.02 g (102.99 mmol) of dimethyl isophthalate and 0.50 g of EDTA-2Na to the inside.Nitrogen gas,Acetone dry ice cooled to -45 C,Control temperature does not exceed -45 C,257mL of 1.0M diisobutyl aluminum hydride toluene solution was added dropwise.After the addition, the reaction is incubated for 2 hours.Temperature control does not exceed 0 C drops 250mL potassium sodium tartrate saturated solution,filter,Liquid separation,The toluene phase is concentrated at 60-70C,Concentrate to 5% of the original volume,There are a lot of solids out,filter,Drying of methyl 3-formylbenzoate 14.20 g at 50CYield 84.02%,98.92% purity.

The synthetic route of 1459-93-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jinan Xuanhong Bio-pharmaceutical Co., Ltd.; Lou Yadong; Li Zhanjiang; (5 pag.)CN107162906; (2017); A;,
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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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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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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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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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Reference of 36692-49-6, 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. 36692-49-6, name is Methyl 3,4-diaminobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of methyl (4-fluorophenyl)(oxo)acetate (50.0 g, 275 mmol) and methyl 3,4- diaminobenzoate (46.9 g, 282 mmol) in ethanol (2.5 L) was heated to reflux for 2 d. The mixture was cooled to rt and most of the ethanol was removed in vacuo to form a thick paste. 0.5 L of THF was added to get a stirrable slurry and the slurry was stirred for 1 h, diluted further with 1 L of ether and solid was collected by filtration (50.0 g, 76.3%) as a mixture of regioisomers.To a solution of methyl 2-(4-fluorophenyl)-3-oxo-3,4-dihydroquinoxaline-6-carboxylate(50.0 g, 168 mmol) (mixture of regioisomers) in THF (0.9 L) and methanol (0.9 L) at rt was added 2.0 M of sodium hydroxide in water (300 mL). The reaction mixture was stirred at 70 C for 2 h. The mixture was allowed to cool slightly and some solids formed. The reaction mixture was filtered while warm to afford a clear orange solution. The filtrate was stirred with mechanic stirring. IN HC1 aqueous solution (~ 450 rtiL) was slowly added (over 15 min) to pH=8. The suspension was stirred for 5 min, filtered, washed with 100 mL of 1:1 MeOH:THF, dried to give a light yellow solid. [In some cases, there is still some undesired isomer present at this point. If so, the material was redissolved in methanol/THF mixture (14 mL per gram of each solvent) and 1 N NaOH (4.2 equivalents), and then reprecipitated to pH = 8 using 1 N HC1. This dissolution/reprecipitation procedure can be repeated until the pure desired regioisomer is obtained.] To the solid was added 300 mL of methanol, 300 mL of THF, and 250 mL of IN NaOH and the resulting solution was stirred by mechanical stirring until dissolved. The resulting solution was adjusted to pH=2.5 by adding IN HC1. The precipitate was collected by filtration, transferred to a round bottom flask using MeOH, evaporated in vacuo, and azeotroped with MeCN. The resulting solid was dried in vacuum pump to give a pure acid product (26.3 g, 55.2%) as a beige powder. LCMS (ESI+): m/z = 285.0 (M+H). H NMR (400 MHz, DMSO-6) delta 13.34 (s, 1H), 12.76 (s, 1H), 8.44 (dd, J= 9.1, 5.8 Hz, 2H), 7.96 – 7.89 (m, 2H), 7.83 (dd, J= 8.4, 1.8 Hz, 1H), 7.35 (t, J= 9.0 Hz, 2H).

The synthetic route of Methyl 3,4-diaminobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; GIGSTAD, Kenneth, M.; CARDIN, David, P.; HIRAYAMA, Takaharu; HIROSE, Masaaki; HU, Yongbo; KAKEI, Hiroyuki; LEE, Hong, Myung; MOTOYAJI, Takashi; NII, Noriyuki; SHI, Zhan; VYSKOCIL, Stepan; WATANABE, Hiroyuki; WO2015/161142; (2015); A1;,
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These common heterocyclic compound, 56741-34-5, name is Methyl 5-amino-2-fluorobenzoate, 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. SDS of cas: 56741-34-5

Dissolve intermediate 1b (0.36g, 1.26mmol) in acetone solution,The reactants 1c (214 mg, 1.26 mmol) and pyridine (0.254 ml, 3.16 mmol) were added sequentially.Then, the reaction solution was heated to reflux at 60 degrees for 2h, and the reaction was monitored by mass spectrometry.The reaction solution was spin-dried and dissolved in ethyl acetate, washed with 1M hydrochloric acid solution in turn,After washing with saturated sodium chloride and drying over anhydrous sodium sulfate, the crude intermediate 1d was obtained.1d crude product was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 5 / 1-2 / 1) to obtain 1d pure product (330mg, yield 62.5%),

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

Reference:
Patent; Fudan University; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; He Yulong; Wang Heyao; Li Yingxia; Dou Huixia; (68 pag.)CN110903224; (2020); A;,
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