Category: esters-buliding-blocks

Some common heterocyclic compound, 581065-95-4, name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, molecular formula is C15H31NO6, 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. Quality Control of tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate

107 mg (0.335 mmol) of tert-Butyl 3-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]propanoate and 93 mg (0.369 mmol) of (2,5-dioxopyrrolidin-1-yl) 2-(2,5-dioxopyrrol-1-yl)acetate were dissolved in 5 ml of dimethylformamide, and 0.074 ml (0.671 mmol) of N-methylmorpholine were added. The reaction mixture was stirred at RT overnight. 0.048 ml (0.838 mmol) of acetic acid were added and the reaction mixture was purified directly by preparative RP-HPLC (column: Reprosil 125*30; 10mu, flow rate: 50 ml/min, MeCN/water/0.1% TFA). The solvents were evaporated under reduced pressure and the residue was dried under high vacuum. This gave 133 mg (86%, purity 100%) of tert-Butyl 3-[2-[2-[2-[2-[[2-(2,5-dioxopyrrol-1-yl)acetyl]amino]ethoxy]ethoxy]ethoxy]ethoxy]propanoate. LC-MS (Method 1): Rt=0.82 min; MS (ESIpos): m/z=459 (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 581065-95-4, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; LERCHEN, Hans-Georg; REBSTOCK, Anne-Sophie; CANCHO GRANDE, Yolanda; WITTROCK, Sven; BERNDT, Sandra; GRITZAN, Uwe; FITTING, Jenny; STELTE-LUDWIG, Beatrix; JONES, Patrick; MAHLERT, Christoph; VOTSMEIER, Christian; SCHOeNFELD, Dorian; TRAUTWEIN, Mark; WEBER, Ernst; PAWLOWSKI, Nikolaus; GREVEN, Simone; GLUeCK, Julian Marius; HAMMER, Stefanie; DIETZ, Lisa; MAeRSCH, Stephan; (357 pag.)US2020/138970; (2020); A1;,
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Reference of 105-53-3,Some common heterocyclic compound, 105-53-3, name is Diethyl malonate, molecular formula is C7H12O4, 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.

Under the protection of nitrogen, the 100g c diethyl malonate, 300 ml anhydrous ethanol into 1000 ml three port in round bottomed flask, under room temperature, adding 40.5g sodium methoxide, then, slowly adding 102.8g bromo n-butane, after adding heating reflux, the reaction 3h; to cool down to room temperature, then adding 40.5g sodium methoxide, then, slowly adding 102.8g bromo-butane, heating reflux reaction 3h. Cooling to room temperature, removing the solvent, by adding 1 mol/L sulfuric acid aqueous solution in the pH value and system to 7 the left and the right, washing the organic phase, is distilled under reduced pressure to obtain the dibutyl c diethyl malonate, 154g (yield 90.6%).

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

Reference:
Patent; Chinese Academy Of Sciences Shanghai Advanced Institute; Jiang Yang; Li Jiusheng; Xu Jian; (6 pag.)CN106748724; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 426-65-3, name is Ethyl Pentafluoropropionate, 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 426-65-3, Computed Properties of C5H5F5O2

Compound 14 (1.2 g, 3.7 mmol) was dissolved in dry toluene (40 mL). Sodium hydride (0.18 g, 40% dispersion in oil) was added, and the mixture was stirred for 15 min at rt. Ethyl pentafluoropropionate (1.1 niL, 7.4 mmol) was added, and the mixture was stirred overnight at rt. Hydrochloric acid (IM, 40 mL) and dichloromethane were added, and the mixure was stirred for 10 min.The organic phase was separated, and the aqueus phase was extracted twice with dichloromethane. The combined organic phases were dried and concentrated. . Purification on silica gel (eluent 10% MeOH in CH2Cl2, v/v) yielded the title compound. 1H NMR (CDCl3): ? 7.71 (2H, d, J 7.9); 7.36 (IH, d, J 3.8); 7.30 (2H, d, J 7.9); 6.73 (IH, d, J 3.4); 6.06 (IH, s); 4.21 (2H, t, / 6.5); 3.12 (2H, m); 2.42 (3H, s).

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; WALLAC OY; WO2009/115644; (2009); A1;,
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Reference of 55666-43-8, The chemical industry reduces the impact on the environment during synthesis 55666-43-8, name is tert-Butyl 3-bromopropanoate, I believe this compound will play a more active role in future production and life.

5. To a solution of alcohol 3 (12.8 g, 40.84 mmol) in toluene (200 ml) was added Bu4NCI (3.7 g, 13.48 mmol). The reaction mixture was cooled to 0 0C after which aqueous 35% NaOH (250 ml) was added followed by a dropwise addition of tert- butyl 3-bromopropionate (4, 8.2 ml, 49.01 mmol) in toluene (50 ml). The mixture was stirred overnight at room temperature. The organic layer was separated and washed with H?O until neutral, dried (Na2SO4), concentrated and co-evaporated with CH2CI2 (3x). Purification by column chromatography (silica, heptane/EtOAc 4:1) gave 5 (11.2 g, 62%) as a yellow oil.

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, tert-Butyl 3-bromopropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRUeNENTHAL GMBH; WO2009/124746; (2009); A1;,
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Reference of 10601-80-6, 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. 10601-80-6, name is Ethyl 3,3-diethoxypropionate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step-a Synthesis of 3,3-diethoxypropanoic acid To a stirred suspension of ethyl 3,3-diethoxypropanoate (15.0 g, 78.88 mmol) in water (32 mL) was added NaOH (4.10 g, 102.6 mmol) and heated to 110 C. for 1.5 h. After completion of the reaction, the reaction mixture was cooled, acidified to pH?3 with aq. 3N HCl and extracted with EtOAc (500 mL*2). The organic layer was washed with water (200 mL), brine (100 mL), dried over sodium sulphate and concentrated. The residue was used for next step without further purification (11.50 g, 91%). 1H NMR (400 MHz, DMSO-d6): delta 12.20 (s, 1H), 4.81 (t, J=5.9 Hz, 1H), 3.58-3.59 (m, 2H), 3.48-3.40 (m, 2H), 2.60-2.40 (m, 2H), 1.09 (t, J=7.3 Hz, 6H).

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

Reference:
Patent; Orion Corporation; SAMAJDAR, Susanta; ABBINENI, Chandrasekhar; SASMAL, Sanjita; HOSAHALLI, Subramanya; (77 pag.)US2016/368906; (2016); 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. 18358-63-9, name is Methyl 4-(methylamino)benzoate, A new synthetic method of this compound is introduced below., SDS of cas: 18358-63-9

For example, some of the silylamines used in the examples below were prepared as follows from the free amine. (i) TMSCI, NEt3, CH2CI2, 17h (ii) a. n-BuLi, THF,-78C, 2 h. b. TMSCL, rt, 17h The silylamines where RN2 is sulfonyl were prepared as follows from a modified amine by heating with bis (trimethylsilyl) trifluoroacetamide (BSTFA). 0 R’ +, 1 MeCN, reflux RW NHTs + I R F CO 3 h, 95%-si- ti – SI- The silylamines were purified by vacuum distillation. Once purified, their were handled under nitrogen at all times, and stored at-20C

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; CAMBRIDGE UNIVERSITY TECHNICAL SERVICES LIMITED; ASTRAZENECA UK LIMITED; WO2005/90283; (2005); 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. 35180-01-9, name is Chloromethyl isopropyl carbonate, A new synthetic method of this compound is introduced below., Formula: C5H9ClO3

Preparation of Compound 167Compound 167. A 20 mL microwave vial was charged with starting acid (300 mg, 0.651 mmol), potassium carbonate (117 mg, 0.847 mmol), sodium iodide (68.3 mg, 18.6 mu, 0.456 mmol), DMF (10 mL) and chloromethyl isopropyl carbonate (119 mg, 0.782 mmol). Heated at 80 C in microwave for 20 min, then the reaction mixture was partitioned between EtOAc and water (80 mL each). The organic layer was separated, washed with water then brine (80 mL each), dried (magnesium sulfate), filtered and concentrated. The resulting residue was purified by MPLC using an Isco Combiflash (40 g column) 0-80% EtOAc in hexanes linear gradient over 24 column volumes at 40 mL/min. Product isolated from column was dissolved in MeCN (10 mL), treated with water (8 mL) then the resulting mixture was frozen and lyophilized. Gave 167 (306 mg, 0.519 mmol, 80%) as a white solid. Analysis carried out by LCMS (60-98% aqueous MeCN, formic acid modifier, 7 min, C4) ESI-MS m/z calc. 576.2869, found 577.57 (M+l)+; Retention time: 3.05 minutes. (1H NMR shows rotamers) 1H NMR (300.0 MHz, DMSO) delta 7.33 (s, 0.55H), 7.24 (s, 0.45H), 5.89 (d, J = 6.3 Hz, 0.55H), 5.81 (dd, J = 6.3, 8.0 Hz, 1H), 5.73 (d, J = 6.3 Hz, 0.45H), 5.58 (t, J = 7.5 Hz, 0.45H), 5.16 (d, J = 2.4 Hz, 0.55H), 4.87 – 4.85 (m, 1H), 3.11 (s, 1.65H), 3.02 (s, 1.35H), 2.85 (s, 1.65H), 2.63 (s, 1.35H), 1.99 – 1.86 (m, 1H), 1.67 – 1.35 (m, 6H), 1.34 – 1.08 (m, 18H) and 0.82 – 0.51 (m, 8H) ppm.

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; VERTEX PHARMACEUTICALS INCORPORATED; GREEN, Jeremy; WILSON, Dean, M.; KONG, Laval, Chan Chun; DAS, Sanjoy, Kumar; POISSON, Carl; COURT, John, J.; TANG, Qing; LI, Pan; COLLIER, Philip, N.; WAAL, Nathan; LAUFFER, David, J.; DORSCH, Warren; WO2012/6055; (2012); A2;,
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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. 39149-80-9, name is tert-Butyl 2-bromopropanoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: tert-Butyl 2-bromopropanoate

General procedure: A solution of NaHMDS (1.0 M in THF, 2.1 mL, 2.1 mmol) was added dropwise to the solution of 15 (R4 and R5 are methyl, 334 mg, 2.0 mmol) in THF (10 mL) at 78 C under argon. After 5 min, a solution of 16 (152 mg, 1.0 mmol) in THF (5 mL) was added dropwise. After another 5 min, the reaction was quenched with saturated ammonium chloride solution. The aqueous phase was extracted with EtOAc (3 20 mL). The combined organic layer was washed with saturated brine and dried over Na2SO4. The solvent was removed under reduced pressure

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 39149-80-9.

Reference:
Article; Li, Qing; Xiao, Fenfen; Wang, Yunxia; Hu, Xiangdong; Synthetic Communications; vol. 46; 12; (2016); p. 1062 – 1067;,
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Synthetic Route of 35450-36-3, 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. 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A sealed tube of 25 mL equipped with a magnetic stir bar was charged with alkynes (0.20 mmol), 2-bromobenzoic esters (0.22 mmol), CuI (0.02 mmol, 10 mol%), NaOH (0.4 mmol, 2 equiv) and CH3CN (1.0 mL). The reaction mixture was stirred at 100 C for 24 h. The reaction was monitored by GC or GC-MS. After completion of the reaction, the reaction mixture was cooled to room temperature, then washed with saturated NH4Cl aqueous solution (5.0 mL), and extracted with CHCl3 (3 * 5.0 mL). The combined organic phases were dried over Na2SO4 (anhydrous), concentrated in vacuum. The crude product was purified by flash column chromatography (eluent: ethyl acetate/petroleum ether = 1/20-1/10) on silica gel to afford the desired product.

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 2-bromo-5-methoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sun, Mengli; Su, Lebin; Dong, Jianyu; Liu, Long; Zhou, Yongbo; Yin, Shuang-Feng; Tetrahedron Letters; vol. 58; 25; (2017); p. 2433 – 2437;,
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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. 5941-55-9, name is Ethyl (E)-3-Ethoxyacrylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl (E)-3-Ethoxyacrylate

To a reactor was charged K3PO4 (4104 g granular, 19.3 moles), ethyl 3-amino-lH-pyrazole-4-carboxylate (2000 g, 12.9 moles), and DMF (18.8 kg) and the mixture was agitated. After 20 min, (?)-ethyl 3- ethoxyacrylate, (2230 g, 15.5 moles) was added and the mixture was heated to 110-115 C internal temperature (IT). After the reaction was judged to be complete based on consumption of starting material , heating was ceased. The mixture was allowed to stir and cool overnight. Aqueous hydrochloric acid (3 M, 13 L) was added over ~ 2 h. DI water (6 L) was added and the mixture was allowed to stir overnight. The mixture was filtered through polypropylene filter cloth (PPFC) and the residue was washed with water (3 x 5 vol, 3 x 10 L). The solid was placed in trays and oven dried under vacuum at 55 C for 3 days and then 45 C for 4 days to constant weight of (2553 g 95.6%).

The synthetic route of 5941-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZHAO, Qian; SPENCER, Stacey; JIANG, Yutong; HAAS, Julia; EARY, Charles Todd; (335 pag.)WO2018/81417; (2018); A2;,
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