Month: August 2021

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. 50624-94-7, name is tert-Butyl ethyl oxalate, A new synthetic method of this compound is introduced below., SDS of cas: 50624-94-7

Isopropylmagnesium chloride (2M in THF, 6.0 ml, 12 mmol) was added dropwise to a solution of bis(2-dimethylaminoethyl)ether (1.92 g, 12.0 mmol) in THF (50 ml) at 0 C and stirred for 15 minutes. 3-Iodobenzonitrile (2.29 g, 10.0 mmol) was added to the reaction mixture and stirred at room temperature for 20 minutes. The resulting reaction solution was added dropwise to tert-butyl ethyl oxalate (J. Org. Chem, 1996, 61, 4530) (1.92 g, 11.0 mmol) in THF (50 ml) at at -10 C and warmed to room temperature for 2 hours. The reaction was quenched with saturated NH4Cl solution (50 ml), extracted with Et2O (100 ml x 2), washed with brine, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica (EtOAc/Hexanes 10/90-30/70) to give tert- butyl 2-(3-cyanophenyl)-2-oxoacetate (892 mg, 39 %).

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; EURO-CELTIQUE S.A.; SHIONOGI & CO., LTD.; WO2008/150447; (2008); A1;,
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Application of 1128-00-3,Some common heterocyclic compound, 1128-00-3, name is Ethyl 2-aminocyclohex-1-enecarboxylate, molecular formula is C9H15NO2, 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 solution of appropriate carboxylic acid 44a-d (1.0 mmol) in dichloromethane (6 ml) oxalylchloride (3.0 mmol) and a drop of DMF were added. The reaction mixture was stirred at ambient temperature for 40 min and the solvent was removed in vacuo. The residue was dissolved in dichloromethane (6 ml), and under argon to the obtained solution was added a mixture of ethyl 2-aminocyclohex-1-enecarboxylate (33) (1.1 mmol) and triethylamine (1.1 mmol) in dichloromethane (3 ml). The reaction mixture was stirred at room temperature for 2 h. The mixture was diluted with dichloromethane, washed successively with NaHCO3 solution, brine, and dried (Na2SO4). The solvent was removed and the residue was purified as indicated below to give crystalline compounds 45a-d.

The synthetic route of 1128-00-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bobileva, Olga; Bokaldere, Rasma; Gailite, Vija; Kaula, Ilze; Ikaunieks, Martins; Duburs, Gunars; Petrovska, Ramona; Mandrika, Ilona; Klovins, Janis; Loza, Einars; Bioorganic and Medicinal Chemistry; vol. 22; 14; (2014); p. 3654 – 3669;,
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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. 108928-00-3, name is Ethyl 2,4-difluorobenzoate, A new synthetic method of this compound is introduced below., name: Ethyl 2,4-difluorobenzoate

The ethyl ester (3a) (3.8 g) was dissolved in fuming nitric acid (3 ml) and concentrated sulfuric acid (3 ml) at 0 C. and stirred for 2.5 hours. Thereafter, the reaction mixture was diluted with water (10 ml) and extracted with dichloromethane (200 ml). The organic phase was washed with a saturated solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (silica gel, hexane:acetic acid ethyl ester: 6:1) and resulted in the desired product (3.96 g).1H NMR (300 MHz, CDCl3): delta: 8.70 (m, 1H), 7.05 (m, 1H), 4.36 (q, 2H), 1.35 (t, 3H)

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; Morphochem Aktiengesellschaft Fur Kombinatorische Chemie; US2010/324030; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 383-62-0,Some common heterocyclic compound, 383-62-0, name is Ethyl 2-chloro-2,2-difluoroacetate, molecular formula is C4H5ClF2O2, 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.

Step 3 – Synthesis of l-(3-(difluoromethoxy)-lH-pyrazol-l-yl)ethanone [0228] To a 250 mL round-bottom flask was added l-(3-hydroxy-lH-pyrazol-l- yl)ethanone (5.0 g, 39.65 mmol, 1.00 equiv), N,N-dimethylformamide (50.0 mL), potassium carbonate (11.0 g, 79.02 mmol, 2.00 equiv) and ethyl 2-chloro-2,2-difluoroacetate (7.5 g, 47.31 mmol, 1.20 equiv). The resulting solution was stirred for 12 h at 60 C, then diluted with water. The resulting mixture was extracted with ethyl ether (3x) and the combined organic layers washed with water, dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was applied onto a silica gel column eluting with ethyl ether/hexanes (0: 100 to 1 : 1) to afford the title compound as colorless oil. 1H-NMR (400 MHz, CDC13): delta 8.15 (d, 1H), 7.02 (t, 1H), 6.14 (d, 1H), 2.62 (s, 3H).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; LYCERA CORPORATION; AICHER, Thomas D.; VAN HUIS, Chad A.; MACLEAN, John K.; ANDRESEN, Brian M.; BARR, Kenneth J.; BIENSTOCK, Corey E.; ANTHONY, Neville J.; DANIELS, Matthew; LIU, Yuan; WHITE, Catherine M.; LAPOINTE, Blair T.; SCIAMMETTA, Nunzio; SIMOV, Vladimir; TROTTER, Wesley, B.; LIU, Kun; WO2015/95788; (2015); A1;,
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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 40876-98-0 as follows. Computed Properties of C8H11NaO5

Step 1: 6-hydroxypyrimidine-4-carboxylic acid; 63.5 g (287 mmol) sodium diethyl-oxalacetate and 30.2 g (287 mmol) formamidine acetate were added to 24.1 g (0.597 mol) NaOH in 3.6 L water. The mixture was stirred overnight at RT. Then activated charcoal was added and the mixture was refluxed for 1 h. It was filtered while hot and after cooling acidified with aqueous HCl. The solution was concentrated to dryness by rotary evaporation. The residue contained the desired product and was used in the next step without any further purification.Yield: 83.0 g

According to the analysis of related databases, 40876-98-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2011/172218; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 344-14-9, 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. 344-14-9, name is Dimethyl 2-fluoromalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

163 mg (2 mmol) of ethylamine hydrochloride, 1.50 g (10 mmol) of dimethyl fluoromalonate, 212 mg (2 mmol) of sodium carbonate and 10 ml of ethanol were added to the reactor,The reaction was stirred at 50 C for 10 hours.Filtration, evaporation of ethanol, the remaining mixture was directly separated by column chromatography,310 mg of methyl alpha- (N-ethyl) carbamoyrifluoroacetate was obtained in a yield95%.

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, Dimethyl 2-fluoromalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Xi’an Modern Chemical Institute; Wang Lun; Lin Shuangzheng; Li Bingbo; Wang Yuemei; Yang Cuifeng; Wu Zongkai; Wei Tianqi; (5 pag.)CN104496737; (2017); B;,
Ester – Wikipedia,
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These common heterocyclic compound, 6627-89-0, name is tert-Butyl phenyl carbonate, 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. Computed Properties of C11H14O3

tert-Butyl 4-(3-formyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate (94e) A solution of tert-butyl 4-bromo-1H-pyrrolo[2,3-c]pyridine-1-carboxylate 94d (1.37 g, 4.61 mmol), 1-tetrahydro-2H-pyran-2-yl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-3-carbaldehyde 36c (1.78 g, 5.00 mmol), and potassium phosphate (1.47 g, 6.92 mmol) in N,N-dimethylacetamide (46 mL) and water (4.6 mL) was degassed by bubbling with N2 for 30 min. Tetrakis(triphenylphosphine) palladium(0) (266 mg, 0.231 mmol) was added, and the mixture was degassed an additional 30 min before placing in a 90 C. oil bath. After 2 hours the reaction was removed from heat, diluted with EtOAc (150 mL), and washed with a mixture of water (100 mL) and saturated aqueous NaHCO3 (100 mL). The aqueous layer was extracted with EtOAc (2*100 mL) and the combined organics were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The crude mixture was dissolved in anhydrous THF (20 mL) and added to a suspension of sodium hydride (307 mg of a 60% suspension in oil) in THF (10 mL) at 0 C. After 20 min stirring, tert-butylphenyl carbonate (1.0 mL, 5.4 mmol) was added and the mixture stirred 20 min before carefully quenching with water (50 mL). The aqueous layer was extracted with EtOAc (3*50 mL) and the combined organics were washed with bring, dried (MgSO4), filtered, and concentrated in vacuo. Silica gel chromatography of the crude residue (eluding with a 10-80% EtOAc in hexanes gradient) afforded 94e (367 mg, 18%) as a yellow foam. 1H NMR (300 MHz, CDCl3) delta 10.30 (s, 1H), 9.42 (s, 1H), 8.56 (s, 1H), 8.54 (s, 1H), 7.83 (m, 2H), 7.74 (dd, J=1.70, 8.67 Hz, 1H), 6.78 (d, J=3.01 Hz, 1H), 5.91 (dd, J=2.64, 8.85 Hz, 1H), 4.05 (m, 1H), 3.83 (m, 1H), 2.62 (m, 2H), 2.23 (m, 2H), 1.84 (m, 2H), 1.73 (s, 9H).

The synthetic route of tert-Butyl phenyl carbonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC; US2005/90529; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 924-99-2, A common heterocyclic compound, 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, molecular formula is C7H13NO2, 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: Ethyl 4-(4-chlorophenyl)-2-thioxo-1,2,3,4-tertahydropyrimidine-5-carboxylate 6a (Table 2, entry 1). To a mixture of thiourea 12a (23.0 mg, 0.302 mmol), 4-chlorobenzaldehyde 13a (63.0 mg, 0.448 mmol), and ethyl 3-dimethylaminoacrylate 9 (64.0 mg, 0.447 mmol) in anhydrous DMF (0.3 mL) was added anhydrous aluminum chloride (8.0 mg, 0.0600 mmol) at room temperature, and the reaction mixture was stirred at 110 C for 3 h. To the mixture was added EtOAc (10 mL) and 1 M HCl aqueous solution (5 mL), and the organic layer was separated. The aqueous layer was extracted with EtOAc (10 mL), and the combined organic layers were washed with water (5 mL) and brine (5 mL), dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography [n-hexane-EtOAc (4:1 to 2:1)] to give 6a (78.9 mg, 0.266 mmol, 88%) as pale yellow crystals.

The synthetic route of 924-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Arai, Rie; Cho, Hidetsura; Gokurakuji, Yuki; Kikuchi, Hidetomo; Kubo, Takanori; Nakamura, Yuri; Nishimura, Yoshio; Sunaga, Katsuyoshi; Yuan, Bo; Tetrahedron Letters; (2020);,
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These common heterocyclic compound, 5445-17-0, name is Methyl 2-bromopropanoate, 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. SDS of cas: 5445-17-0

(No.)-Cis-2- ( 4-[4-(acetyl-phenyl-amino)-2-methyl-3 ,4-dihydro-2H-quinoline- I -carbonyl]- phenylamino} -propionic acid methyl ester was prepared from (No.)-cis-N-[1-(4-amino-benzoyl)-2- methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide. A mixture of (No.)-cis-N-[1-(4- amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide (210 mg, 0.53 mmol), potassium carbonate (123 mg, 0.89 mmol), and methyl 2-bromopropionate (70 uL, 0.63mmol) in dry dimethylformamide (2 mL) was heated at 100C for 6h, then cooled to room temperature and stirred with 20ml water until all of the salts dissolved. The aqueous layer was separated and was extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting oil was purified by silica gel chromatography, eluting with (97: 3 methylene chloride/methanol) to afford the title compound (220 mg, 87%). ‘H-NMR (CDC13) 8: 1.2 (4H, m), 1.4 (3H, d), 2.0 (3H, s), 2.3 (1H, br), 3.7 (3H, s), 4.1 (1H, m), 4.7 (1H, m), 5.6 (1H, br), 6.3 (2H, d), 6.6 (1H, d), 6.9 (1H, m), 7.0 (2H, d), 7.3-7.4 (7H, m). MS m/z: 487 (M+2).

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

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2005/100321; (2005); 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 36692-49-6 as follows. Product Details of 36692-49-6

A mixture of methyl 3,4-diaminobenzoate (8, 830 mg, 5 mmol) and 4-methoxy benzaldehyde (9a, 680 mg, 5 mmol) in ethanol (25 mL) was heated with an aqueous solution of sodium pyrosulfite (1.42 g, 1.5 mmol, 5 mL) and then refluxed for 4-6 h, until TLC indicated that the reaction was complete. The ethanol was evaporated under vacuum and the residue was dissolved in CHCl3 (2 * 15 mL) and washed with water. The combined organic phases were dried over anhydrous Na2SO4, and the solvent was removed under vacuum and purified by column chromatography MeOH-CH2Cl2 (0.5:9.5) to obtain the pure product 10a as a white solid (952 mg, 68%); mp: 231-234 C; 1H NMR (500 MHz, CDCl3): delta 8.28 (s, 1H), 8.12 (d, J = 9.1 Hz, 2H), 7.92 (d, J = 9.0 Hz, 1H), 7.12 (d, J = 8.3 Hz, 1H), 6.98 (d, J = 8.3 Hz, 2H), 3.94 (s, 3H), 3.85 (s, 3H); MS (ESI): m/z 283 [M + H]+.

According to the analysis of related databases, 36692-49-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kamal, Ahmed; Nagaseshadri; Nayak, V. Lakshma; Srinivasulu, Vunnam; Sathish, Manda; Kapure, Jeevak Sopanrao; Suresh Reddy; Bioorganic Chemistry; vol. 63; (2015); p. 72 – 84;,
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