Month: December 2020

581065-95-4, 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. 581065-95-4, name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, A new synthetic method of this compound is introduced below.

118 mg (566 mumol) of N-[(benzyloxy)carbonyl]glycine were initially charged in 5.0 ml of DMF, 200 mg (622 mumol) of tert-butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, 130 mg (849 mumol) of 1-hydroxy-1H-benzotriazole hydrate and 130 mg (679 mumol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added and the mixture was stirred at RT for 1 h. Ethyl acetate was added and the mixture was extracted twice with 5% citric acid solution and with saturated sodium hydrogencarbonate solution. The organic phase was washed twice with saturated sodium chloride solution and dried over magnesium sulphate. The solvents were evaporated under reduced pressure and the residue was dried under high vacuum. This gave 274 mg (95% of theory) of tert-butyl 1-({N-[(benzyloxy)carbonyl]glycyl}amino)-3,6,9,12-tetraoxapentadecan-15-oate. LC-MS (Method 12): Rt=1.69 min; MS (ESIpos): m/z=513 (M+H)+.

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; BAYER PHARMA AKTIENGESELLSCHAFT; LERCHEN, Hans-Georg; REBSTOCK, Anne-Sophie; MARX, Leo; JOHANNES, Sarah Anna Liesa; STELTE-LUDWIG, Beatrix; DIETZ, Lisa; TERJUNG, Carsten; MAHLERT, Christoph; GREVEN, Simone; SOMMER, Anette; BERNDT, Sandra; (481 pag.)US2019/77752; (2019); A1;,
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105-53-3, A common compound: 105-53-3, name is Diethyl malonate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

EXAMPLE 28 The following experiment demonstrates the in situ preparation of the onium compound in the process. In a reaction flask were added 137.5 g (1.1 mol) trans 1,4-dichlorobutene-2, 160.0 g (1.0 mol) diethyl malonate, 600 cc methylene chloride and 6.8 g (5 mol % based on diethyl malonate) N,N-dimethylbenzylamine. The mixture was stirred at ambient temperature for 20 minutes and 124.8 g (2.0 mol) flaked 90% potassium hydroxide then added in small portions over a one-hour period while maintaining the reaction temperature at 25 C. with external cooling. The reaction was then stirred at ambient temperature for four hours. Diethyl 2-vinylcyclopropane-1,1-dicarboxylate (126.6 g; 59.8% yield) was obtained.

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, Diethyl malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Emery Industries, Inc.; US4252739; (1981); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

18595-18-1, The chemical industry reduces the impact on the environment during synthesis 18595-18-1, name is Methyl 3-amino-4-methylbenzoate, I believe this compound will play a more active role in future production and life.

j00646j A solution of methyl 3-amino-4-methylbenzoate (25 g, 151 mmol) in ethanol (62 mL) was charged with 70% conc. HNO3 (9.5 g, 151 mmol) and solution of cyanamide (9.5 g, 227 mmol) in water (25 mL) at room temperature. The resulting solution was heated to 90Cfor 16 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL) and stirred for 30 mm. The solid precipitated out was filtered, washed with ethyl acetate:diethyl ether and dried to give 28.6 g, 70% yield of the title compound as yellow solid. ?H NMR (400 MHz, DMSO-d6): oe = 9.33 (br. s, 1 H), 7.87 (dd, J= 7.94, 1.32 Hz, 1 H), 7.75 (d, J = 1.32 Hz, 1 H), 7.51 (d, J= 8.38 Hz, 1 H), 7.30 (s, 4 H), 3.86 (s, 3 H), 2.28 (s, 3 H); MS (ESj:m/z = 208.15 [M+H], 249 [M+ACN] LCMS: tR = 0.71, 0.79 mm.

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

Reference:
Patent; COFERON, INC.; FOREMAN, Kenneth, W.; JIN, Meizhong; WANNER, Jutta; WERNER, Douglas, S.; WO2015/106292; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

35180-01-9, Adding a certain compound to certain chemical reactions, such as: 35180-01-9, name is Chloromethyl isopropyl carbonate, 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 35180-01-9.

41.4 g of Tenofovir monohydrate (commercially available or prepared as disclosed in CN1264387A) was added to 164 g of N-methylpyrrolidone at 20~25 C.,Then added under stirring triethylamine 40g, 20 ~ 25 C under stirring for 0.5 hours,Chloromethyl isopropyl carbonate was added 100g, warmed to 55-65 C incubated for 5 hours;Stop heating, cooling to 20 ~ 30 C, adding ethyl acetate 320g, purified water 180g,0 ~ 5 C under stirring after the separation, the lower layer and then 110g of ethyl acetate at 0 ~ 5 C under extraction,Combined ethyl acetate layer, purified water 0 ~ 5 C washed twice, each 320g,30 ~ 35 C concentrated ethyl acetate; cyclohexane was added to the concentrate 150mL,20 ~ 25 C under stirring for 10 hours, filtered, cyclohexane 20mL rinse,Tenofovir disoproxil, white solid.

According to the analysis of related databases, 35180-01-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Pan Xusong; Xiao Ning; Wang Yong; Xiang Zhixiang; Lu Chongyu; Jia Xiaoman; Luo Jie; Zheng Wei; (74 pag.)CN103626803; (2017); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

816-27-3, These common heterocyclic compound, 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, 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.

A mixture of l-amino-3-[tert-butyl(dimethyl)silyl]oxy-5-(cyclopropylmethyl)pyrrolidin-2-one (7.1 g, 24.96 mmol) and ethyl 2-ethoxy-2-imino-acetate (9.1 g, 62.4 mmol) in ethanol (150 mL) was stirred at 90 C for 12 h and concentrated under reduced pressure to afford crude (Z)-ethyl 2-amino-2-((3- ((tert-butyldimethylsilyl)oxy)-5-(cyclopropylmethyl)-2-oxopyrrolidin-l-yl)imino) acetate (9.2 g, 96%) as yellow oil. LC-MS RT = 0.783 min, m/z = 384.3 [M+H]+. LCMS (5 to 95%o acetonitrile in water + 0.03%o trifluoacetic acid over 1.5 mins) retention time 0.783 min, ESI+ found [M+H] = 384.3.

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 816-27-3.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; HAMILTON, Gregory; ZHAO, Guiling; CHEN, Huifen; DANIELS, Blake; STIVALA, Craig; (358 pag.)WO2019/12063; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 1731-86-8, name is Methyl undecanoate, I believe this compound will play a more active role in future production and life. 1731-86-8

General procedure: The succinic Gemini surfactants, dl- and meso-2,3-bis(alkyl)succinic acids, were synthesized by the oxidative coupling of enolates of fatty acid esters with copper(II) bromide according to Quermann et al. [35] and subsequent deprotection of ester groups. Following is a typical synthesis of di-tert-butyl 2,3-bis(undecyl)succinate, 2e: first of all, tert-butyl tridecanoate 1e was prepared from tert-butanol, tridecanoic acid, dicyclohexyl carbodiimide (DCC) and DMAP (0.2 equiv) in toluene under stirring at room temperature. In a dry 100 mL flask equipped with a dropping funnel, septum inlet, and magnetic stirrer, a solution of 12.5 mL of lithium diisopropylamide (2.0 M in hexane/THF) and 30 mL of dry THF were added under nitrogen. Under cooling at -78 C, 25 mmol of 1e in 10 mL dry THF was added dropwise over a period of 30 min, and then the mixture was stirred for an additional 15 min. With vigorous stirring 5.0 g of anhydrous CuBr2 powder was added all at once to the solution. After stirring for 30 min, the reaction was quenched by adding 50 mL of 1 M HCl at this temperature, and the mixture was allowed to reach room temperature. After extracting twice with hexane (75 mL each), the combined organic layer was washed with water and dried over Na2SO4. By means of a short path vacuum distillation apparatus, both unreacted ester and alpha-bromo ester (5e) were distilled off (*160 C,1 mmHg). The residue was subjected to column chromatography on silica eluting with hexane/diethyl ether(20:1) to separate dl- (dl-2e) and meso-isomers (meso-2e) at the yields of 36 and 25 %, respectively. Other dl- and meso-isomers of 2a-2g were also prepared in a similar manner, and diastereomers (dl and meso) were separated by SiO2 chromatography.

The chemical industry reduces the impact on the environment during synthesis 1731-86-8. I believe this compound will play a more active role in future production and life.

Reference:
Article; Kawase, Tokuzo; Kagawa-Ohara, Maiko; Aisaka, Tsunetomo; Oida, Tatsuo; Journal of Surfactants and Detergents; vol. 18; 4; (2015); p. 615 – 627;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

35180-01-9,Some common heterocyclic compound, 35180-01-9, name is Chloromethyl isopropyl carbonate, molecular formula is C5H9ClO3, 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 chloromethyl isopropyl carbonate (5.02 g, 32.77 mmol) in MeCN (20mL) was added Nal (14.74 g, 98.31 mmol). The reaction mixture was stirred at 60 00 for 3 hr. Themixture was then concentrated and the residue was dissolved in DCM (300 mL). The resulting mixture was washed with sat. Na25203 (100 mLx2), and the organic phase was dried and concentrated to give 22.2 (7.90 g, 99% yield). 1H NMR (400 MHz, 0D013): oe5.95 (s, 2H), 4.96 (m, 1H), 1.33 (d, J= 6.4 Hz,6H).

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

Reference:
Patent; UNITY BIOTECHNOLOGY, INC.; BACKES, Bradley; W. VON GELDERN, Thomas; CHEN, Bing; (121 pag.)WO2017/101851; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 57486-68-7, name is Methyl 2-chlorophenylacetate, I believe this compound will play a more active role in future production and life. 57486-68-7

General procedure: The oil was thendissolved in EtOH, and NH2NH2.H2O (3 eq) was added.The mixture was refluxed for 10 h. CH2Cl2 (30 mL) was thenadded and extracted with distilled H2O (3 ¡Á 20 mL). Theorganic phase was separated, dried on anhydrous Na2SO4,and evaporated under vacuum to afford correspondinghydrazide 7a in very good yield (white solid, 1.02g, 93%)

The chemical industry reduces the impact on the environment during synthesis 57486-68-7. I believe this compound will play a more active role in future production and life.

Reference:
Article; Vu, Vu Van; Nhung, Trinh Thi; Thanh, Nguyen Thi; Chinh, Luu Van; Tien, Vu Dinh; Thuy, Vu Thu; Thi Thao, Do; Nam, Nguyen Hai; Koeckritz, Angela; Vu, Tran Khac; Journal of Chemistry; vol. 2017; (2017);,
Ester – Wikipedia,
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A common heterocyclic compound, 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate, molecular formula is C10H11BrO2, 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. 14062-25-0.

Example 46A(+/-)-Ethyl (4-bromophenyl)(cyclopentyl)acetate; Under an atmosphere of argon, 5.54 g (49.4 mmol) of potassium tert-butoxide were dissolved in 100 ml of DMF, and the mixture was cooled to 0 C. 10 g (41.1 mmol) of ethyl 4-bromophenylacetate, dissolved in 20 ml of DMF, were then added. The reaction mixture was stirred at 0 C. for 30 min, and 5.29 ml (49.4 mmol) of cyclopentyl bromide were then added dropwise. The mixture was stirred at 0-5 C. for 1 h and then added to water (1 litre) and extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated. This gave 12.41 g (97% of theory) of the title compound in the form of a yellowish oil.LC-MS (Method 5): Rt=1.44 min; m/z=311/313 (M+H)+.1H-NMR (400 MHz, DMSO-d6): delta [ppm]=0.89-1.04 (m, 1H), 1.05-1.69 (m, 9H), 1.72-1.86 (m, 1H), 2.34-2.48 (m, 1H), 3.37 (d, 1H), 3.92-4.17 (m, 2H), 7.24-7.37 (m, 2H), 7.44-7.57 (m, 2H).

The synthetic route of Ethyl 2-(4-bromophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/172448; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, 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 653-92-9, 653-92-9

General procedure: Method A:16,17 A two-necked round-bottomed flask equipped with a reflux condenser and a magnetic stir bar was charged with the 2-bromobenzoic acid (20mmol) and freshly distilled methanol (25mL). The solution was heated in a hot water bath, conc. H2SO4 (8mmol) was added slowly and the reaction mixture was refluxed for 24h. After cooling to room temperature around half of the amount of the solvent was removed in vacuo and the residue was partitioned between water (50mL) and diethyl ether (70mL). The organic layer was separated and washed with saturated NaHCO3 (2¡Á50mL), water (50mL) and brine (50mL), dried over anhydrous MgSO4 and the volatiles were removed under reduced pressure. The crude product thus obtained was purified by flash chromatography on silica gel to afford the alkyl-2-halobenzoate. (0023) In a two-necked round-bottomed flask equipped with a reflux condenser and a magnetic stir bar the alkyl 2-halobenzoate (22.5mmol) was dissolved in freshly distilled dry THF (30mL) under argon. The solution was cooled to 0C using an ice bath and NaH (60% in mineral oil, 15mmol) was added portionwise. After stirring for 15min a solution of the alkyl acetate (15mmol) in dry THF (30mL) was added dropwise to the reaction mixture at 0C. The mixture was warmed up, stirred at room temperature for 2h and heated under reflux for 24h. After cooling to room temperature around half of the amount of the solvent was removed in vacuo and the reaction mixture was diluted with toluene (50mL). The resulting mixture was washed with 2N HCl (50mL), saturated NH4Cl (50mL), dried over anhydrous MgSO4 and the volatiles were removed under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford the alkyl 3-(2?-halophenyl)-3-oxo-propanoate 1.

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-4-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Weischedel, Heike; Sudheendran, Kavitha; Mikhael, Alevtina; Conrad, Juergen; Frey, Wolfgang; Beifuss, Uwe; Tetrahedron; vol. 72; 24; (2016); p. 3454 – 3467;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics