Month: January 2021

Application of 2216-92-4, A common heterocyclic compound, 2216-92-4, name is N-Phenylglycine Ethyl Ester, molecular formula is C10H13NO2, 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.

EXAMPLE 2 Ethyl alpha-(N-pyrrolyl)-phenylacetate 52.8 g (0.24 mole) of ethyl phenylglycinate were dissolved in 136 ml of glacial acetic acid. Thereafter 39 g (0.24 mole) of 2,5-diethoxytetrahydrofuran were added over 10-15 minutes with stirring. The mixture was heated under reflux for one hour. After this time had elapsed, the mixture was allowed to cool and the major portion of the acetic acid was drawn off under reduced pressure. Finally, the residue was distilled under vacuum and the fraction distilling out at 115-118 C. at 0.2 mm Hg was collected. The product obtained was first a colourless oil which crystallized on cooling, adopting a waxy aspect and weighing 46.5 g (70%). M.p. 51-53 C. Centesimal composition: 73.31% C.; 6.08% N; 6.53% H. The IR spectrum in 0.5% KBr is illustrated in FIG. 1.

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; Antibioticos, S.A.; US4563477; (1986); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2065-23-8, name is Methyl 2-phenoxyacetate, 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 2065-23-8, HPLC of Formula: C9H10O3

General procedure: An aqueous CH3CN solution (CH3CN54 ml, H2O 6 ml) of N-Boc Val-OMe1a (0.6 mmol, 10 mM), phenanthrene(0.6 mmol, 10 mM), 1,4-dicyanobenzene (0.6 mmol, 10 mM) and NaOH (3 mmol, 50 mM)in three Pyrex vessels (18 mm x 180 mm) was purged with argon for 10 min andadded by acrylonitrile 2a (0.6 mmol,10 mM) under argon atmosphere. The mixture was heated by water bath at 40 for 2h and irradiated with a 100-W high-pressure mercury lamp for 3 h at roomtemperature. Then the mixture was evaporated, and the resulting residue wasdissolved in EtOAc and washed with water, dried over Na2SO4,and concentrated under reduced pressure. The product was purified by silica gelcolumn chromatography using hexane and EtOAc as eluents to give adduct 3a

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:
Article; Saito, Hikaru; Kanetake, Takayuki; Osaka, Kazuyuki; Maeda, Kousuke; Morita, Toshio; Yoshimi, Yasuharu; Tetrahedron Letters; vol. 56; 13; (2015); p. 1645 – 1648;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1236357-65-5, name is Methyl 1-(4-bromophenyl)cyclobutanecarboxylate, molecular formula is C12H13BrO2, 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: Methyl 1-(4-bromophenyl)cyclobutanecarboxylate

Step 1. Methyl l-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)cyclobutane-l -carboxylate: Into a 40 ml vial equipped with a magnetic stir bar and under N2 were added 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2- dioxaborolane (2.26 g, 8.92 mmol), methyl l-(4-bromophenyl)cyclobutanecarboxylate (2 g, 7.43 mmol), Pd(dppf)C12, complex with DCM (307.18 mg, 371.56 muiotatauiotaomicron) and potassium acetate (2.19 g, 22.29 mmol). The vial was evacuated under vacuum and refilled with N2. DMF (15 mL) was added, and the mixture was degassed for 10 minutes with N2 and then heated to 100 C O/N. The black reaction mixture was cooled to RT, and purified by column chromatography through silica gel eluting with 100:0 to 0: 100 Hexanes:EtOAc as a gradient over 25 minutes. The desired fractions were combined, concentrated and further dried under high vacuum O/N to provide a yellow solid (1.6 g) LCMS (ESI+) m/z = 317 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1236357-65-5, its application will become more common.

Reference:
Patent; TEMPEST THERAPEUTICS, INC.; POWELL, David Andrew; ROPPE, Jeffrey Roger; SEIDERS, Thomas Jon; DING, Jinyue; SHENG, Tao; JACINTHO, Jason Duarte; (65 pag.)WO2019/79614; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 620-72-4 as follows. Quality Control of Phenyl 2-bromoacetate

To a solution of phenylbromoacetate (18.58 g, 86 mmol) in CH3CN under nitrogen was added a solution of (R)-phenylglycinol (10.17 g, 74 mmol) and di-isopropylethylamine (34 ml_, 195 mmol) in CH3CN. The volatiles were removed under reduced pressure keeping the bath temperature below 25 0C to obtain an oil that was treated with EtOAc (120 mL) and stirred for 15 min. The resulting white precipitate was removed by filtration. The filtrate was concentrated under reduced pressure and the desired product was isolated using column chromatography (SiO2) with a step gradient of 10 percent to 50 percent [v/v] EtOAc in cyclohexane to give after evaporation (f?)-5-phenylmorpholin-2- one EBE 06134 (3.17 g, 24 percent yield) as a white solid.MW: 177.2; Yield: 24 percent; White Solid; Mp (0C): 50.3Rf\ 0.30 (EtOAc:cyclohexane = 50:50). 1H-NMR (CDCI3, delta): 1.99 (s, 1 H, NH), 3.89 (q, 2H, J = 17.8 Hz, N-CH2), 4.18(dd, 1 H, J = 3.7 Hz, J = 10.3 Hz, 0-CH), 4.29 (t, 1 H, J = 10.5 Hz, N-CH), 4.40(dd, 1 H, J = 3.7 Hz, J = 10.5 Hz, 0-CH), 7.30-7.45 (m, 5H, ArH).13C-NMR (CDCI3, delta): 46.8, 54.8, 72.8, 125.3 (2xC), 127.0, 127.3 (2xC), 135.9,166.0. [G]22D = + 30.3 ¡ã (c = 1.00, MeOH).

According to the analysis of related databases, 620-72-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALLERGAN, INC.; WO2008/11478; (2008); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 344-14-9, 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. 344-14-9, name is Dimethyl 2-fluoromalonate, This compound has unique chemical properties. The synthetic route is as follows.

Dimethyl 2-fluoromalonate (77.00g, 0.80mol, 2.0eq.) Was dissolved in 1L of tetrahydrofuran, cooled to -40 , 1M NaHMDS tetrahydrofuran solution (800mL, 0.80mol, 2.0eq. ), After stirring for 1h, add 400mL of a compound of formula (50g, 0.40mol, 1.0eq.) In tetrahydrofuran solution 400mL, return to room temperature after completion of the dropwise reaction for 2h, add 500mL of saturated ammonium chloride aqueous solution to separate, organic The phase was washed with saturated brine, dried, concentrated, column chromatography (petroleum ether / ethyl acetate), and concentrated to obtain 99.7 g of the compound of formula III, with a yield of 45.1%.

The chemical industry reduces the impact on the environment during synthesis Dimethyl 2-fluoromalonate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Nanjing Furunkaide Bio-pharmaceutical Co., Ltd.; Zhang Leiliang; Xu Feng; (16 pag.)CN110963955; (2020); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 756525-95-8,Some common heterocyclic compound, 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, molecular formula is C11H23NO4, 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 stirred solution of carboxylic acid 10 (30 mg, 0.125 mmol), HATU (53 mg, 1.38 mmol) and DIPEA (70 L, 0.375 mmol) in DMF (5 mL) at 25 C was added the corresponding primary amine (33 mg, 0.138 mmol). The reaction mixture was stirred for 16 h, diluted with 0.1 N aqueous NaOH (15 mL) and extracted with CH2C12 (3 x 20 mL). The combined organic phases were dried over anhydrous Na2S04 and concentrated under reduced pressure. The residue was purified by flash column chromatography (0-5 % MeOH in DCM) to give compound M (18 mg, 0.040 mmol, 32% yield). MS (ESI) m/z 456 (M+H)+

The synthetic route of 756525-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; THE GENERAL HOSPITAL CORPORATION D/B/A MASSACHUSETTS GENERAL HOSPITAL; GRAY, Nathanael S.; HAGGARTY, Stephen J.; CAI, Quan; TELO BAPTISTA LIMA DA SILVA, Maria Catarina; ZHANG, Tinghu; FERGUSON, Fleur M.; (220 pag.)WO2019/14429; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 89-71-4, A common heterocyclic compound, 89-71-4, name is Methyl 2-methylbenzoate, molecular formula is C9H10O2, 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.

Placed in a 20L reaction vessel was petroleum ether, o-methyl benzoate, N- bromosuccinimide. Use a water bath to control temperature at 15 deg.C. Under stirring, react for 2.5h. Using known separation methods, separated o halomethyl benzoate.

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; Suzhou Huanghe Pharmaceutical Co., Ltd.; Su, Zixuan; Qu, Xiaoming; Xiao, Zuhua; (16 pag.)CN105330639; (2016); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1150566-27-0, name is Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, 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 1150566-27-0, category: esters-buliding-blocks

To a suspension of ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate (I-7) (128 mg, 0.565 mmol) in DMSO (2.5 mL) was added (3S)-3-(tert-butyldimethylsilyloxy)-2-(3-fluorophenyl)pyrrolidine (I-53) (167 mg, 0.565 mmol) and potassium floride (328 mg, 5.65 mmol). The mixture was heated at 120 C. overnight. The mixture was poured into water and extracted with EtOAc twice. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography on silica gel with EtOAc/hexanes gradient as eluant to yield ethyl 6-((3S)-2-(3-fluorophenyl)-3-hydroxypyrrolidin-1-yl)imidazo[1,2-b]pyridazine-3-carboxylate (I-54). MS m/z 371.1 (M+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, Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IRM LLC; US2012/65184; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 14273-90-6, name is Methyl 6-bromohexanoate, 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 14273-90-6, Quality Control of Methyl 6-bromohexanoate

(1) 1,2,3,4-Tetrahydroquinoline (0.50 mL, 3.98 mmol) and methyl 6-bromohexanoate (0.76 mL, 4.78 mmol) were added to MeCN (30 mL) containing KI (1.59 g, 9.58 mmol) and K2CO3 (1.10 g, 7.96 mmol) dissolved therein, and the suspension was stirred at 100 C. for 21 hours in an argon atmosphere. The reaction solution was cooled to room temperature and then diluted with water, followed by extraction with ethyl acetate. The organic phase was washed with saturated saline, dried over Na2SO4, and dried under reduced pressure. The residue was purified by flash column chromatography (hexane/EtOAc=100/0 to 80/20) to obtain N-methoxycarbonylpentyl-1,2,3,4-tetrahydroquinoline (1.10 g, 100%). Colorless oil; 1H NMR (500 MHz, CDCL3) delta: 7.02 (t, J=7.5 Hz, 1H), 6.91 (d, J=7.5 Hz, 1H), 6.51-6.54 (m, 2H), 3.66 (s, 3H), 3.20-3.26 (m, 4H), 2.73 (t, J=6.3 Hz, 2H), 2.31 (t, J=7.5 Hz, 2H), 1.90-1.94 (m, 2H), 1.63-1.69 (m, 2H), 1.56-1.62 (m, 2H), 1.32-1.38 (m, 2H); LRMS (ESI): m/z calcd [M+H]+ 262.2, found 262.0.

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; JAPAN SCIENCE AND TECHNOLOGY AGENCY; KANAI, Motomu; SOMA, Yohei; TANIGUCHI, Atsuhiko; SHIMIZU, Yusuke; (45 pag.)US2017/197956; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

927-68-4, name is 2-Bromoethyl acetate, 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. Quality Control of 2-Bromoethyl acetate

To a solution of the product of step 1(143 mg, 0.69 mmol) in DMF (1.5 mL) at 0 C, wasadded NaH (60% suspension in mineral oil, 30 mg, 0.76 mmol). The mixture was stirred for 0.5 h followed and 2-bromoethyl acetate (184 mg, 0.12 mL, 1.1 mmol) was added. The reaction was brought to room temperature and stirred overnight. The mixture was diluted with EtOAc, washed with water and brine, dried over Na2504, and concentrated underreduced pressure. The residue was purified by silica gel column chromatography (0-20% gradient MeOH in CH2C12) to afford the title compound (180 mg, 89%) as a colorless oil.?H NMR (500 MHz, CDC13) oe 1.36 (t, J=7.4 Hz, 3H), 1.89-2.00 (m, 2H), 2.03-2.15 (m, 5H), 2.75-2.82 (m, 2H), 2.89 (t, J=6.3 Hz, 2H), 3.99 (q, J=7.4 Hz, 2H), 5.25 (s, 2H)

The synthetic route of 927-68-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; GERASYUTO, Aleksey, I.; ARNOLD, Michael, A.; CHEN, Guangming; KARP, Gary, Mitchell; QI, Hongyan; TURPOFF, Anthony, A.; WANG, Jiashi; WOLL, Matthew, G.; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Maria, L.; (374 pag.)WO2016/109706; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics