Month: August 2021

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., name: tert-Butyl 2-bromopropanoate

CS2CO3 (622mg, l.9lmmol) was added to a stirred mixture of tert- butyl 3-(5,6- dimethoxythieno[3,2-b]pyridin-2-yl)-3-oxopropanoate (322mg, 0.954mmol) in DMF (3mL) at 25C. A mixture of fer/-butyl 2-bromopropanoate (2l0mg, l.OOmmol) in DMF (lmL) was added dropwise to the reaction mixture. The reaction mixture was stirred at RT for 5 hours. Additional /er/-butyl 2-bromopropanoate (63mg, 0.030mmol) was added, and the reaction mixture was stirred for 1 hour. Additional /er/-butyl 2-bromopropanoate (63mg, 0.030mmol) was added, and the reaction mixture was stirred overnight. The reaction mixture was diluted with isopropyl acetate (75mL) and sodium citrate (10% w/v in H20, 40mL). The layers were separated, and the aqueous layer was extracted with additional isopropyl acetate (40mL). The organic layers were combined, washed with brine, dried over anhydrous Na^SCri. filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluting EtOAC in Hex) to afford di-/er/-butyl 2-(5,6-dimethoxythieno[3,2-b]pyridine-2- carbonyl)-3-methylsuccinate. LCMS (C23H32NO7S) (ES, m/z): 466 [M+H]+.

According to the analysis of related databases, 39149-80-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; CASH, Brandon, D.; CUMMING, Jared, N.; DEMONG, Duane, E.; HAIDLE, Andrew, M.; JEWELL, James, P.; LARSEN, Matthew, A.; LU, Min; OTTE, Ryan, D.; TAOKA, Brandon, M.; TROTTER, Benjamin Wesley; TRUONG, Quang, T.; (97 pag.)WO2019/195063; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 37466-90-3, These common heterocyclic compound, 37466-90-3, name is Ethyl 3,4-diaminobenzoate, 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.

General procedure: To a mixture of 2-pyridine aldehyde (5a, 107 mg, 1mmol) and 1,2-diaminobenzene (6a, 108 mg, 1 mmol) in ethanol (25 mL)was added an aqueous solution of sodium pyrosulfite (1.52g, 8 mmol, 5 mL) and refluxed for 4 to 6 h, until the TLC indicated that reaction was completed. The reaction mixture was concentrated under vacuum and the residue was dissolved in CHCl3 (2 x15 mL) and washed with water. The combined organic phases were dried over anhydrousNa2SO4, filtered and the solvent was removed under vacuumand purified by column chromatography (70% EtOAc-hexane) to afford compound 7a as a brown solid.

The synthetic route of 37466-90-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kamal, Ahmed; Pogula, Praveen Kumar; Khan, Mohammed Naseer Ahmed; Seshadri, Bobburi Naga; Sreekanth, Kokkonda; Medicinal Chemistry; vol. 9; 5; (2013); p. 651 – 659;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, 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. category: esters-buliding-blocks

[0511] 5-Chlorosalicylaldehyde (20.02 g, 0.128 mole) and ethyl 4,4, 4-trifluorocrotonate (23.68 g, 0.14 mole) were dissolved in anhydrous DMF, warmed to 60 C and treated with anhydrous K2CO3 (17.75 g, 0. 128 mole). The solution was maintained at 60 C for 20 hours, cooled to room temperature, and diluted with water. The solution was extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous MGS04, filtered and concentrated in vacuo to afford 54.32 g of an oil. The oil was dissolved in 250 mL of methanol and 100 mL of water, whereupon a white solid formed that was isolated by filtration. The resulting solid was washed with water and dried in vacuo, to afford the ester as a yellow solid (24.31 g, 62%): mp 62-64 C. 1H NMR (CDC13/90 MHz) 7.64 (s, 1H), 7.30-7. 21 (m, 2H), 6.96 (d, 1H, J= Hz), 5.70 (q, 1H, J= Hz), 4.30 (q, 2H, J= 7.2 Hz), 1.35 (t, 3H, J=7.2 Hz).

The synthetic route of 25597-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); A1;,
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. 56741-34-5, name is Methyl 5-amino-2-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 56741-34-5

General procedure: To a solution of 11a (500 mg, 1.85 mmol) in acetone (10 mL) was added 12 (380 mg, 1.85 mmol) and pyridine (0.45 mL, 5.54 mmol).The mixture was stirred at 55 C for 1 h. The mixture was concentrated,diluted with ethyl acetate and washed with 1M HCl and brine twice.Then, the ethyl acetate layer was dried over anhydrous sodium sulfate andconcentrated to give the crude product. The crude product was purified bysilica column eluting with petroleum ether/ethyl acetate (5/1-2/1) to givethe desired product (0.33 g, yield 44.3%) as grey solid

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 56741-34-5.

Reference:
Article; He, Yulong; Dou, Huixia; Gao, Dingding; Wang, Ting; Zhang, Mingming; Wang, Heyao; Li, Yingxia; Bioorganic and Medicinal Chemistry; vol. 27; 19; (2019);,
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 5335-05-7 as follows. category: esters-buliding-blocks

Under nitrogen protection,The racemic mixture of 3- (indol-3-yl) -butyric acid or S-3-iv)(0 · 20 g, 1 mmol)And triethylamine (0 · 10 g, 1 mmol)Dissolved in DMF solution (6ml) solution at room temperature for 5min,Then methyl chlorobenzoate (0.17 g, 1 mmol),The reaction at room temperature 24h, after the reaction was added ethyl acetate 50ml,The ethyl acetate layer was washed with water (80 ml X 3) and the ethyl acetate layer was dried over anhydrous Na 2 SO 4. After the solvent was removed by column chromatography, the target compound 3- (3-indol-3-yl) Methyl ester (0.23 g, 70%),Which is a racemic mixture or (S) isomer.

According to the analysis of related databases, 5335-05-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Bio-technology Institute; Liu Zongying; Li Zhuorong; Jin Jie; Zhu Juntai; (111 pag.)CN103664996; (2017); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 383-62-0, The chemical industry reduces the impact on the environment during synthesis 383-62-0, name is Ethyl 2-chloro-2,2-difluoroacetate, I believe this compound will play a more active role in future production and life.

To a solution of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.5 g, 2.58 mmol, 1 eq) in DMF (5 mL) was added ethyl 2-chloro-2,2-difluoro-acetate (490.20 mg, 3.09 mmol, 392.16 uL, 1.2 eq) and K2CO (712.26 mg, 5.15 mmol, 2 eq). The mixture was stirred at 60 C for 16 h. The reaction mixture was poured into H2O 10 mL, and extracted with EtOAc (10 mL x 3). The combined organic layers were washed with brine (10 mL x 2), dried over Na2SO4, filtered and concentrated under reduced pressure to afford the title compound (0.3 g, crude) as yellow solid, which was used into the next step without further purification. The structure was confirmed by 1H NMR and HOSEY.

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 2-chloro-2,2-difluoroacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MARINEAU, Jason, J.; ZAHLER, Robert; CIBLAT, Stephane; WINTER, Dana, K.; KABRO, Anzhelika; ROY, Stephanie; SCHMIDT, Darby; CHUAQUI, Claudio; MALOJCIC, Goran; PIRAS, Henri; WHITMORE, Kenneth, Matthew; LUND, Kate-Iyn; SINKO, Bill; SPROTT, Kevin; (418 pag.)WO2018/13867; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 2905-67-1, 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. 2905-67-1, name is Methyl 3,5-dichlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 25 g of 3,5-dichlorobenzoic acid methyl and 22.5 g of trifluoromethyltrimethylsilane in 300 g of dimethoxyethane, 0.37 g of cesium fluoride was added with ice-cooling and the mixture was warmed to room temperature and stirred for 4 hours. After disappearance of the raw material was confirmed, 200 g of water was put into the reaction solution to extract with 200 g of ethyl acetate. After the organic layer was dehydrated and dried with saturated saline followed by anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 35.5 g of 1-(3,5-dichlorophenyl)-2,2,2-trifluoro-1-trimethylsilyloxy-1-methoxyethane as yellow liquid matter.

The chemical industry reduces the impact on the environment during synthesis Methyl 3,5-dichlorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Nissan Chemical Industries, Ltd.; EP1975149; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 59247-47-1, A common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-bromobenzoate, molecular formula is C11H13BrO2, 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.

General procedure: Under nitrogen atmosphere, a mixture of alcohol 1a (28.6 mg, 0.10 mmol, 1.0 equiv), 4-bromoanisole (37.4 mg, 0.20 mmol, 2.0 equiv), [C12H8NH2PdCl]2 (1.5 mg, 2.5 mol%), L10 (13.6 mg, 15 mol%) and NaH (7.2 mg, 0.30 mmol, 3.0 equiv) in anhydrous toluene (2.0 mL), were heated at 80C for 12 h. After being cooled to room temperature, the solvent was removed and the residue was purified by flash chromatography on silica gel (hexanes/ethyl acetate = 30:1) to afford the desired product 2a (38.0 mg, 97%, 96% ee).

The synthetic route of 59247-47-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Deng, Ruixian; Xi, Junwei; Li, Qigang; Gu, Zhenhua; Chem; vol. 5; 7; (2019); p. 1834 – 1846;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 581065-95-4, 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. 581065-95-4, name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

00345] tert- butyl 2-((2-(2,6-dioxopiperidin-3-yl)-l,3-dioxoisoindolin-4-yl)oxy)acetate (0775) (0.06rng, 0.13mmol) was dissolved in 1 ml. TFA. The solution was stirred at room temperature for 2 hours. Then the mixture was concentrated under reduced pressure to afford solid product, which was used in the following synthesis without further purification. Then the product from last step (0.043g, 0.13mmol) was mixed with HATH (0.099g, 0.26mmol) in 2mL DMF with the presence of EtsN (9luL, G.65mrnol). The mixture was stirred for lOmin before amino PEG-4-i-butyl ester (0.042g, O.lSmmol) was added. The reaction was stirred at room temperature for 5 hours. The mixture was next subjected to direct preparative HPLC purification to afford 97mg product (>100%) LCMS (ESI) m/z 580.22 (show as free acid instead of t-butyl ester) [(M+H)+; calcd for C^TTfiNsOii : 636.28]

The synthetic route of tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BUHRLAGE, Sara; ANDERSON, Kenneth C.; HIDESHIMA, Teru; GRAY, Nathanael S.; LIU, Xiaoxi; (137 pag.)WO2019/118728; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 581065-95-4,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.

To 2-{3-[(2-{5-[(3a5,45,6aR)-2-oxo-hexahydro- 1 H-thieno[3,4-d]i midazolidin-4- yl]pentanamido}ethyl)carbamoyl]-5-[3, 5-bis(carboxymethoxy)phenyl]phenoxy}acetic acid(Preparation 5, 20.0 mg, 29.0 pmol) dissolved in DMF (500 pL) was added HATU (44.0 mg,116 pmol) and DIPEA (40.5 pL, 232 pmol). After 1 minute tert-butyl 1-amino-3,6,9,12- tetraoxapentadecan-15-oate (35.0 pL, 116 pmol) was added and the reaction was stirred at room temperature under nitrogen for 3 hours. The reaction was concentrated in vacuo and purified using reverse phase column chromatography (Biotage SP1, 4 g, 0-18 column, elutingwith 5-40% MeCN in water with 0.1% NH3) to afford the title compound as a colourless oil (30.9 mg, 67%).LCMS Method B: Rt = 2.96 mins, ES MS mlz 599.7 [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 tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, its application will become more common.

Reference:
Patent; CENTAURI THERAPEUTICS LIMITED; PICKFORD, Christopher; WATSON, Christine; GLOSSOP, Melanie; (189 pag.)WO2017/60729; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics