Category: esters-buliding-blocks

Electric Literature of 3618-04-0,Some common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, molecular formula is C9H16O3, 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 1 : To a stirred solution ethyl 4-hydroxycyclohexanecarboxylate (2.78 g, 16.0 mmol, 1 equiv.) in dry THF (80 mL), was added dropwise lithium aluminum hydride (1 M in THF, 24 mL, 24.0 mmol, 1 .5 equiv.) at 0¡ãC under azote atmosphere. The reaction mixture was warmed to room temperature and stirred for 3h30. The mixture was then cooled to 0¡ãC and water (1 ml_), 15percent aqueous sodium hydroxide (1 mL) and water (3 mL) were successively added. The mixture was allowed to warm to room temperature and stirred overnight. The salts were filtered through a pad of celite and the filtrate was dried over Na2S04 and concentrated under vacuum to yield 4- (hydroxymethyl)cyclohexanol (2.10 g, quant.) as a colorless oil.

The synthetic route of 3618-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BCI PHARMA; SURLERAUX, Dominique; AMIABLE, Claire; GUILLON, Remi; (239 pag.)WO2017/191297; (2017); A1;,
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These common heterocyclic compound, 20372-66-1, name is Methyl 2,4,5-trifluorobenzoate, 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. HPLC of Formula: C8H5F3O2

To a solution of 5-chloro-[1,1?-biphenyl]-2-ol (5.0 g, 24.4 mmol) in anhydrous dimethyl sulfoxide (50 mL) was added potassium carbonate (5.1 g, 36.6 mmol) and methyl 2,4,5-trifluorobenzoate (4.4 g, 24.4 mmol) and the reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was partitioned between ethyl acetate (400 mL) and water (100 mL), and the organic phase washed with water (50 mL x 2), brine (50 mL); dried over anhydrous sodium sulfateand concentrated in vacuo to yield the title compound as a colorless foam (8.9 g, quant. yield): ?HNMR (300 MHz, CDC13) oe 7.61 (dd, J = 10.9, 6.6 Hz, 1H), 7.48-7.42 (m, 3H), 7.37-7.26 (m, 4H), 7.05 (d, J = 8.6 Hz, 1H), 6.39 (dd, J = 11.1, 6.6 Hz, 1H), 3.85 (s, 3H).

The synthetic route of Methyl 2,4,5-trifluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; XENON PHARMACEUTICALS INC.; ANDREZ, Jean-Christophe; BERGERON, Philippe; BICHLER, Paul, Robert; CHOWDHURY, Sultan; DEHNHARDT, Christoph, Martin; FOCKEN, Thilo; GONG, Wei; GRIMWOOD, Michael, Edward; HASAN, Abid; HEMEON, Ivan, William; JIA, Qi; SAFINA, Brian; SUN, Shaoyi; WILSON, Michael, Scott; ZENOVA, Alla, Yurevna; (436 pag.)WO2016/7534; (2016); A1;,
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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. 14064-10-9, name is Diethyl 2-chloromalonate, A new synthetic method of this compound is introduced below., Computed Properties of C7H11ClO4

DBU (4.64 g, 30.5 mmol) was added at room temperature to a solution of 8 (7.00 g, 27.7 mmol) and diethyl chloromalonate (6.47 g, 33.2 mmol) in DMF (70 ml). After stirring at this temperature for 24 h, the reaction mixture was quenched with H2O (200 ml) at 0 ¡ãC. The aqueous layer was extracted with AcOEt (200 ml ¡Á 2). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane-AcOEt) to give 9 (4.67 g, 50percent) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta 1.38 (3H, t, J = 7.1 Hz), 1.47 (9H, s), 1.87-1.95 (2H, m), 2.38-2.49 (1H, m), 2.74-2.87 (2H, m), 4.10-4.28 (2H, m), 4.35 (2H, q, J = 7.1 Hz), 4.50 (2H, br s), 7.06 (1H, s).

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:
Article; Koshizawa, Tomoaki; Morimoto, Toshiharu; Watanabe, Gen; Watanabe, Toshiaki; Yamasaki, Nao; Sawada, Yoshikazu; Fukuda, Tomoaki; Okuda, Ayumu; Shibuya, Kimiyuki; Ohgiya, Tadaaki; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3249 – 3253;,
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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. 1130165-74-0, name is Ethyl 4-bromo-3-fluorobenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 1130165-74-0

Preparation Example 20 A mixture of ethyl 4-bromo-3-fluorobenzoate (1 g), cyclopropylboronic acid monohydrate (643 mg), tetrakistriphenylphosphinepalladium (235 mg), potassium phosphate (3.1 g), toluene (10 ml), and water (1 ml) was thoroughly stirred at 110 C. overnight. To the reaction mixture was added water, followed by carrying out a separation of the layers using ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was crudely purified by silica gel column chromatography (hexane:ethyl acetate=85:15), and then to a mixture of the crude product, THF (20 ml), and MeOH (20 ml) was added a 1 M aqueous sodium hydroxide solution (20 ml), followed by stirring at room temperature overnight. To the reaction mixture was added 1 M hydrochloric acid (20 ml), followed by concentrating under reduced pressure to remove the organic solvent. The precipitated solid was collected by filtration to obtain 600 mg of 4-cyclopropyl-3-fluorobenzoic acid as a colorless solid.

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; ASTELLAS PHARMA INC.; US2012/46292; (2012); A1;,
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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. 1186-73-8, name is Trimethyl methanetricarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Trimethyl methanetricarboxylate

A mixture of N-benzyl-2-(3,6-dihydro-2H-pyran-4-yl)-7-isopropyl-3-(3-methoxypropoxy)-7,8-dihydrooxepino[3,2-b]pyridin-9(6H)-imine (600 mg, 1.29 mmol), trimethylmethanetricarboxylate (491 mg, 2.58 mmol) in Ph20 (3 mL) was degassed under vacuum and purged with nitrogen gas (cycle repeated 3 times). The mixture was stirred at 220 C for 15 min under nitrogen atmosphere. The mixture was cooled to rt and purified directly by normal phase S1O2 chromatography (0-50% EtO Ac/petroleum ether) to give methyl 11-benzyl-2-(3,6-dihydro-2H-pyran-4-yl)-8-hydroxy-7-isopropyl-3-(3-methoxypropoxy)-10-oxo-6,7,10,11-tetrahydrooxepino[3,2-b:4,5-b’]dipyridine-9-carboxylate as a yellow oil (430 mg, 56% yield, m/z: 591 [M+H] observed).

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; ARBUTUS BIOPHARMA, INC.; CHEN, Shuai; DORSEY, Bruce D.; FAN, Yi; GOTCHEV, Dimitar B.; QUINTERO, Jorge; (252 pag.)WO2019/177937; (2019); 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 13671-00-6 as follows. Safety of Methyl 2,6-difluorobenzoate

Example 43A 2,6-Difluorophenyl)(2H2)methanol At 0 C., 1.00 g (5.81 mmol) of methyl 2,6-difluorobenzoate were initially charged in 20 ml of THF, and 11.62 ml of (11.62 mmol) of lithium aluminium deuteride [=LiAlD4=lithium tetrahydrido(2H4)aluminate](1 M solution in THF) were added dropwise. The mixture was stirred for 1 h in an ice bath that slowly thawed. 0.58 ml of water, 0.58 ml of 2 N aqueous sodium hydroxide solution and 1.16 ml of water were then added in succession to the reaction solution. The precipitate formed was filtered off and washed thoroughly with THF. The filtrate was concentrated and the residue was dried under high vacuum. This gave 0.743 g of the product (88% of theory, purity about 90%), which was reacted further without purification. LC-MS (Method 14): Rt=2.38 min MS (EIpos): m/z=146 (M)+ 1H NMR (400 MHz, DMSO-d6): delta=5.20 (s, 1H), 7.08 (t, 2H), 7.39 (quint, 1H).

According to the analysis of related databases, 13671-00-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; HARTUNG, Ingo; FOLLMANN, Markus; JAUTELAT, Rolf; STRAUB, Alexander; HAssFELD, Jorma; LINDNER, Niels; SCHNEIDER, Dirk; WUNDER, Frank; STASCH, Johannes-Peter; REDLICH, Gorden; LI, Volkhart Min-Jian; BECKER-PELSTER, Eva Maria; KNORR, Andreas; US2014/128386; (2014); A1;,
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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. 3153-37-5, name is Methyl 4-chlorobutyrate, A new synthetic method of this compound is introduced below., COA of Formula: C5H9ClO2

EXAMPLE 1 Methods for the preparation of the compounds of the invention are disclosed in U.S. Pat. No. 6,147,250. The following is a method of producing Compound A. Probucol (5, 9.69 mmol) and methyl 4-chlorobutyrate (3.1 g. 1.4 eq) were stirred in DMF (15 mL) and potassium fluoride on alumina (7 g, 5 eq) was added. The mixture was stirred at room temperature under nitrogen for 20.5 hours. It was filtered, diluted with ethyl acetate (100 mL), washed with water and brine, dried over sodium sulfate, and evaporated. Chromatography (MPLC, 10% to 80% of dichloromethane in hexanes) gave 0.98 g of methyl 4-[4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenoxy]butyrate. Methyl 4-[4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenoxy]butyrate (0.95 g, obtained above) was dissolved in THI/MeOH/H2O (4:1;1, 15.4 mL) and lithium hydroxide hydrate (0.19 g) was added. The mixture was stirred at room temperature for four hours and then acidified with 0.3 N HCl. The mixture was poured into brine and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and evaporated to give 0.60 g of 4-[4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenoxy]butyric acid (Compound A) as a solid.

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; Edwards, David B.; Somers, Patricia K.; Glass, Mitchell; US2002/156022; (2002); A1;,
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Reference of 24812-90-6, A common heterocyclic compound, 24812-90-6, name is Methyl 3-amino-4-methoxybenzoate, molecular formula is C9H11NO3, 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.

Step 1: 4-Methoxy-3-(4-nitro-phenoxycarbonylamino)-benzoic acid methyl ester. To a stirred, cooled (0 C.) solution of methyl-3-amino-4-methoxy benzoate (5.0 g; 27.6 mmol) in methylene chloride (100 mL) was added pyridine (2.34 mL; 29 mmol) followed by 4 nitrophenyl chloroformate (5.8 g; 29 mmol). After stirring for 8 hours, the reaction was diluted with methylene chloride (100 mL), washed with IN hydrochloric acid (2*125 mL), 10% aqueous sodium carbonate (2*125 mL), brine (1*125 mL), then dried (MgSO4), and filtered. The filtered material was concentrated under reduced pressure. The residue was taken up in ethyl acetate (100 mL) followed by hexanes (700 mL). A precipitate formed which was filtered to yield an off white solid (80% yield).

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; Keegan, Kathleen S.; Kesicki, Edward A.; Gaudino, John Joseph; Cook, Adam Wade; Cowen, Scott Douglas; Burgess, Laurence Edward; US2003/69284; (2003); A1;,
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7270-63-5, name is 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione, 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. HPLC of Formula: C6H6N2O4

General procedure: To a solution of diazo compound 1 (0.5 mmol) and alkynes (1.1 mmol) in toluene (2 mL) was added rhodium(II) pivalate (0.01 mmol). The reaction mixture was stirred at 60C for 0.5-5 h. The solvent was evaporated in rotary evaporator under reduced pressure to give the residue. The residue was purified by flash column chromatography on silica gel to give the product. 4.2.13. 2,4-Bis(4-(trifluoromethyl)phenyl)-6H-furo[2,3-b]pyran-6-one (5l). Reaction of 1 (85 mg, 0.5 mmol) and 4-ethynyl-alpha,alpha,alpha-trifluorotoluene (187 mg, 1.1 mmol) under Rh2(OPiv)4 (6 mg, 0.01 mmol) afforded 5l (106 mg, 50%) as a solid: mp 158-160 C; 1H NMR (300 MHz, CDCl3) delta 7.82 (2H, d, J=8.1 Hz), 7.76-7.73 (4H, m), 7.65 (2H, d, J=8.1 Hz), 6.94 (1H, s), 6.26 (1H, s); 13C NMR (75 MHz, CDCl3) delta 158.6, 152.1, 147.3, 138.4, 131.9, 128.2, 127.9, 126.4, 126.3, 126.3, 126.1, 126.0, 125.1, 123.7, 106.4, 102.4, 99.5; IR (KBr) 3125, 1728, 1616, 1528, 1325, 1127, 837, 672 cm-1; HRMS m/z (M+) calcd for C21H10F6O3: 424.0534. Found: 424.0532.

The synthetic route of 7270-63-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Somai Magar, Krishna Bahadur; Lee, Yong Rok; Kim, Sung Hong; Tetrahedron; vol. 69; 44; (2013); p. 9294 – 9302;,
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Reference of 344-14-9, The chemical industry reduces the impact on the environment during synthesis 344-14-9, name is Dimethyl 2-fluoromalonate, I believe this compound will play a more active role in future production and life.

General procedure: [Pd(C3H5)Cl]2 (0.004 mmol, 4 mol%), [6-(allyloxymethyl)-N-(2-((R)-((S)-1-(3,5-dimethoxyphenyl)propyl)sulfinyl)phenyl)picoli-namide] (6b, 0.008 mmol, 8 mol%), and (E)-1,3-disubstituted allyl acetates 7 (0.1 mmol) were dissolved in THF (2.0 mL) in a dry Schlenk tube filled with argon. The reaction mixture was stirred for 30 min at room temperature. Then Cs2CO3 (3.0 equiv) and dimethyl 2-fluoromalonate 8 (0.3 mmol, 3.0 equiv) were added. After the completion of the reaction monitoring by TLC, the crude reaction mixture was filtrated with celite and the solvent was removed under reduced pressure. The crude residue was purified by flash column chromatography (petroleum ether/ethyl acetate) to give the desired products 9.

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:
Article; Zhang, Min; Zhao, Mingzhu; Zheng, Purui; Zhang, Hongbo; Zhao, Xiaoming; Journal of Fluorine Chemistry; vol. 189; (2016); p. 13 – 21;,
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