Tag: M.W=100-200

Electric Literature of 3618-04-0, The chemical industry reduces the impact on the environment during synthesis 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, I believe this compound will play a more active role in future production and life.

EXAMPLE 5 5-Butyl-9-[1-(4,6-dimethyl-pyrimidine-5-carbonyl)-4-methyl-piperidin-4-yl]-3-(trans-4-hydroxy-cyclohexylmethyl)-1-oxa-3,9-diaza-spiro[5.5]undecan-2-one (I-4) 4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexanecarboxylic acid ethyl ester (38)-To a solution of 4-oxy-cyclohexanecarboxylic acid ethyl ester (CASRN 17159-80-7, 1.7 g, 0.01 mol) in DMF (14 mL) was added DMAP (58 mg, 0.47 mmol), TEA (1.54 mL) and tert-butyl-dimethylsilyl chloride (1.65 g, 0.011 mol). The reaction mixture was stirred at RT for 18 h, poured into ice (10 g), extracted with EtOAc (3*50 mL). The organic extracts were dried (MgSO4) filtered and concentrated. The residue was purified by SiO2 chromatography eluding with EtOAc/hexane (1:20) to afford 2.25 g (79%) of 4-(tert-butyl-dimethyl-silanyloxy)-cyclohexanecarboxylic acid ethyl ester (38) as colorless 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, trans-Ethyl 4-hydroxycyclohexanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Rotstein, David Mark; Melville, Chris Richard; US2008/249087; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 32122-09-1, name is Ethyl 2-(benzyloxy)acetate, 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 32122-09-1, Safety of Ethyl 2-(benzyloxy)acetate

To a solution of ethyl 2-(benzyloxy)acetate (1.30 g, 6.69 mmol) in anhydrous THF (30 mL) at -78 C was added dropwise LDA (2.0 M, 4.40 mL). The mixture was stirred for 30 min, and then tert-butyl 4-oxopiperidine-l-carboxylate (1.15 g, 5.77 mmol) in anhydrous THF (20 mL) was added. The mixture was stirred at -78 C for 1 hour, then quenched with sat aqueous H4CI (30 mL) and extracted with EtOAc (50 mLx3). The combined organic extracts were washed with brine and dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column (25% EtOAc in pet ether) to give the desired product as a colorless oil (1.82 g). Yield 80% (95% purity, UV=214 nm, ESI 294.1 (M+H)+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-(benzyloxy)acetate, and friends who are interested can also refer to it.

Reference:
Patent; LAZULI, INC.; HARRISON, Bryce, Alden; BURSAVICH, Matthew, Gregory; GERASYUTO, Aleksey, Lgorevich; HAHN, Kristopher, Neil; KONZE, Kyle, David; LIN, Fu-Yang; LIPPA, Blaise, Scott; LUGOVSKOY, Alexey, Alexandrovich; ROGERS, Bruce, Nelsen; SVENSSON, Mats, Ake; TROAST, Dawn, Marie; (0 pag.)WO2018/160522; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 14062-19-2, name is Ethyl p-Tolylacetate, molecular formula is C11H14O2, 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. COA of Formula: C11H14O2

LiHMDS was prepared by the treatment of HMDS (2.432 g, 15.07 mmol) with n-BuLi (1.6 M solution in hexane, 9.4 mL, 15 mmol) in dry THF (30 mL) at 0C for 30 min. To a solution of ethyl p-tolylacetate (1.778 g, 9.98 mmol) in dry THF (30 ml) was added the LiHMDS at -78C. The mixture was stirred at -78C for 30 min. To the mixture, ethyl cyanoformate (1.110 g, 11.20 mmol) was added at -78C, and then the mixture was allowed to warm to 0C for 80 min. 10% HCl was added at 0C, and the mixture was extracted twice with CH2Cl2. The combined organic extracts were dried over Na2SO4. After removal of the solvent, the residue was purified by column chromatography using silica gel (hexane/acetone 25/1) to afford 7 as a colorless oil (2.396 g, 96%). 1H NMR spectra data were identical to those reported in the literature.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 14062-19-2, its application will become more common.

Reference:
Article; Kawasaki, Masashi; Kuroyanagi, Saki; Ito, Takuya; Morita, Hiroyuki; Tanaka, Yasuo; Toyooka, Naoki; Tetrahedron; vol. 73; 15; (2017); p. 2089 – 2099;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 431-47-0, name is Methyl 2,2,2-trifluoroacetate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

Synthesis Example 40 Synthesis of N-propargyltrifluoroacetamide Propargylamine (Aldrich, 25 g, 0.45 mol) was added dropwise to methyl trifluoroacetate (Tokyo Chemical Industry Co., Ltd., 69.2 g, 0.54 mol) cooled to 0 C. They were allowed to react at 0 C. for two hours to afford 43.8 g (86.0%) of N-propargyltrifluoroacetamide after purification by vacuum distillation (23 mmHg, boiling point; 77 C.).

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; The Institute of Physical and Chemical Research; US6365350; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 23680-40-2, A common heterocyclic compound, 23680-40-2, name is Methyl 3-bromopropiolate, molecular formula is C4H3BrO2, 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 solution of 2-methylfuran (15.7mL, 174 mmol) andmethyl 3-bromopropiolate 11 (7.10 g, 43.6 mmol) incyclohexane (100 mL) was refluxed for 1 d. Afterremoval of the solvent, the resulting mixture of 12aand 12b was used in the next step without purification.12a: 1H NMR (300 MHz, CDCl3) delta 1.89 (3H, s),3.79 (3H, s), 5.21 (1H, d, J = 1.8 Hz), 6.99 (1H, d,J = 5.1 Hz), 7.14 (1H, dd, J = 1.8, 5.1 Hz); 13C NMR(75 MHz, CDCl3) delta 16.43, 51.65, 87.98, 91.49, 142.12,146.96, 149.94, 153.89, 163.49.The ratio of 12a:12b was determined to be 11:1based on 1H NMR analysis. The signal due to 1-Me of12b was observed at delta = 1.74.

The synthetic route of 23680-40-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Konishi, Shunsuke; Mori, Naoki; Takikawa, Hirosato; Watanabe, Hidenori; Bioscience, Biotechnology and Biochemistry; vol. 83; 3; (2019); p. 391 – 399;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 87661-20-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 87661-20-9 name is tert-Butyl cyclopropanecarboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

c) 1 -r(2S,5R)-5-r4-(3-Methoxy-propyl)-2,2-dimethyl-3,4-dihvdro-2H- benzori ,41oxazin-6-ylmethoxy1-1 -(toluene-4-sulfonyl)-piperidin-2-ylmethyl1- cvclopropanecarboxylic acid tert-butyl ester; A solution of 5.00 mmol of cyclopropanecarboxylic acid tert-butyl ester [87661 -20-9] in 50 ml of tetrahydrofuran at -78C is treated with 5.5 mmol of lithium diisopropyl- amine. The reaction mixture is stirred at -78C for 4 hours before the addition of a solution of 6.00 mmol of 6-[(3R,6S)-6-bromomethyl-1 -(toluene-4-sulfonyl)-piperidin-3- yloxymethyl]-4-(3-methoxy-propyl)-2,2-dimethyl-3,4-dihydro-2H-benzo[1 ,4]oxazine in 10 ml of tetrahydrofuran. The reaction is stirred at -78C for 1 hour, then allowed to warm to room temperature over 4 hours, and quenched with saturated aqueous ammonium chloride solution. The mixture is extracted with tert butyl-methyl ether (3x), the combined organic extracts are dried with sodium sulfate, and concentrated under reduced pressure. The residue is purified by flash chromatography (SiO2 60F) to afford the title compound, which is identified based on the Rf value.

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

Reference:
Patent; NOVARTIS AG; WO2009/106599; (2009); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, molecular formula is C7H13NO2, 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. name: Ethyl 3-(dimethylamino)acrylate

General procedure: All microwave reactions were carried out in a capped (10 mL) microwave-vessel (Borosilicate glass vial sealed) that was placed in a microwave cavity. The pressure was set at 17 bar (average of an effective pressure = 4 bar) with power 75 W. DIEA (3.4 g, 3.4 mmol) was added to a solution of either 2,5-difluoro-4-(pyrrolidin-1-yl) benzoylchloride 12 (0.83 g, 3.4 mmol) or 2,5-difluoro-4-(pyrrolidin-1-yl)benzothioyl chloride 13 (0.88 g, 3.4 mmol) and ethyl-3-(diethylamino)acrylate 14 (0.45 g, 3.1 mmol) in acetonitrile (5 mL). The mixture reaction was held at 100 C for 20 min. After the reaction vessel was cooled to room temperature, the crude product was diluted with water (10 mL) and extracted with ethyl acetate(3 × 10 mL). The organic layers were combined, dried over Na2SO4, filtered, evaporated and purified by a flash column chromatography (eluent n-hexane: acetone, 3:1)to give the titled compounds.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 924-99-2, its application will become more common.

Reference:
Article; Almashal, Faeza A.; Alshawi, Jasim M.; Dhumad, Adil M.; Jassem, Ahmed M.; Medicinal Chemistry Research; (2020);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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

Tenofovir (60 g, 0.209 mol) was placed in a 500 ml four-necked flask.250 g of N-methylpyrrolidone, and triethylamine (62.3 g, 0.617 mol) was added with stirring.Additional tetrabutylammonium bromide (40.25 g, 0.125 mol) was added.Warming up to 50 C,At this temperature, chloromethyl isopropyl carbonate (63.5 g, 0.418 mol) was added dropwise.Investment,Keep warm for 5 to 10 hours,After the end of the heat preservation, after extracting twice with n-heptane 250 ml×2, the water was separated into 480 g of purified water, and extracted three times with isopropyl acetate 240 g+120 g+120 g, and the isopropyl acetate solution was combined and washed twice with an aqueous solution of 180 g×2. , concentrated to dryness under reduced pressure at 40 C, 60 g of isopropanol, 40 CConcentrated to dryness under reduced pressure, adding 100 g of isopropanol, heating and dissolving, cooling to -10 to -20 C, adding 0.5 g of seed crystals, keeping for 2-8 hours, suction filtration,The wet product was dried at 40 C under reduced pressure to obtain tenofovir (99.28 g).Yield 91.5%The purity is 98.3%.

The synthetic route of 35180-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Jiuzhou Pharmaceutical Co., Ltd.; Ye Meiqi; Xu Jiankang; Wu Hao; Chen Linguo; Ye Kai; (17 pag.)CN104974188; (2019); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 2-(bromomethyl)acrylate

General procedure: A mixture of (E)-3-phenyl-2-[(toluene-4-sulfonylamino)methyl]-acrylic acid methyl ester (345 mg, 1.0 mmol), methyl 2-(bromomethyl)acrylate (269 mg, 1.5 mmol), and K2CO3(276 mg, 2.0 equiv) in DMF (3.0 mL) was stirred at room temperature for 5 h. After removal of the solvent and column chromatographic purification process (hexanes/Et2O, 5:1) compound 1a was obtained as a white solid, 401 mg (90%). Other compounds 1b-m were prepared analogously, and the spectroscopic data of 1a-m are as follows.

According to the analysis of related databases, 4224-69-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kim, Ko Hoon; Lim, Jin Woo; Moon, Hye Ran; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 35; 11; (2014); p. 3254 – 3260;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 4934-99-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 4934-99-0 name is Methyl 3-hydroxycyclobutanecarboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: To a flask containing alcohol (3 equiv.) in THF (0.1 – 0.5 M) at 0 C was added sodium hydride (3 equiv. 60% oil immersion). The resulting slurry was stirred 10 min and the alkyl bromide (1 equiv.) was added. The reaction mixture was allowed to reach rt and was stirred 2 h at which point NH4CI solution (saturated, 10 mL) was added followed by EtOAc (10 mL). The layers were separated, and the aqueous layer was extracted with EtOAc (3 x 10 mL). The combined organic layers were dried over anhydrous MgSOr, filtered and concentrated under reduced pressure and purified employing either silica gel flash chromatography (0-> I 00% EtO Ac/hexanes) or reverse-phase preparatory HPLC (Phenomenex Luna 10 m C18, 100A,150 x 30 mm, 5 ->95% MeCN (0.1% formic acid) in H2O, 25 min, 60 mL/min) to afford the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-hydroxycyclobutanecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; DENALI THERAPEUTICS INC.; CRAIG, Robert A., II; DE VICENTE FIDALGO, Javier; ESTRADA, Anthony A.; FENG, Jianwen A.; FOX, Brian M.; LEXA, Katrina W.; OSIPOV, Maksim; SWEENEY, Zachary K.; THOTTUMKARA, Arun; (137 pag.)WO2019/183589; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics