Month: March 2021

Adding a certain compound to certain chemical reactions, such as: 6914-71-2, name is 1,1-Cyclopropanedicarboxylic acid dimethyl ester, 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 6914-71-2, Application In Synthesis of 1,1-Cyclopropanedicarboxylic acid dimethyl ester

Synthesis of Cyclopropane-1,1-dicarboxylic acid methyl ester KOH (42 mg, 0.75 mmol) was added to a solution cyclopropane-1,1-dicarboxylic acid dimethyl ester (100 mg, 0.63 mmol) in methanol. The resulting mixture was stirred for 4 hours at ambient temperature then concentrated. The residue was diluted with water, acidified with conc. HCl and the product was extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford 65 mg (71%) of cyclopropane-1,1-dicarboxylic acid methyl ester.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1-Cyclopropanedicarboxylic acid dimethyl ester, and friends who are interested can also refer to it.

Reference:
Patent; FOREST LABORATORIES HOLDINGS LIMITED; US2009/239848; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 35179-98-7, These common heterocyclic compound, 35179-98-7, name is Chloromethyl ethyl 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.

ELQ-300 (0.85 g, 1.8 mmol), tetrabutylammonium iodide (1.33 g, 3.6 mmol) and potassium carbonate (0.50 g, 3.6 mmol) were dissolved anhydrous dimethylformamide (8 ml) in a flame-dried round bottom flask at 60 C under inert atmosphere. Chloromethyl ethyl carbonate (0.5 g, 3.6 mmol) was added dropwise and the reaction stirred under inert atmosphere at 60 C for two hours, at which point reaction completion was confirmed by thin layer chromatography. After cooling to room temperature, the reaction solvent was removed under reduced pressure and the mixture taken up in water (10 ml) and extracted with dichloromethane (3 x 20 ml). Combined organic layers were washed with brine (10 ml), dried over MgS04, and the dichloromethane evaporated under reduced pressure. The resulting crude product was purified by flash chromatography (EtOAc/DCM) to yield the title compound, ELQ- 331, as a white crystalline solid (560 mg, 54%). 1H NMR (400 MHz, DMSO-d6): delta = 7.98 (s, 1H), 7.57 (s, 1H), 7.44 (m, 4H), 7.21 (m, 4H), 5.76 (s, 2H), 5.35 (s, 2H), 4.03 (s, 3H), 2.44 (s, 3H), 1.11 (t, 3H, J = 7.1 Hz); M.P. (C): 103.5-103.7.

Statistics shows that Chloromethyl ethyl carbonate is playing an increasingly important role. we look forward to future research findings about 35179-98-7.

Reference:
Patent; OREGON HEALTH & SCIENCE UNIVERSITY; THE UNITED STATES GOVERNMENT AS REPRESENTED BY THE DEPARTMENT OF VETERANS AFFAIRS; RISCOE, Michael; NILSEN, Aaron; STICKLES, Allison; MILEY, Galen; WINTER, Rolf; POU, Sovitj; LI, Yuexin; KELLY, Jane Xu; FORQUER, Isaac; DOGGETT, J. Stone; BRUZUAL, Igor; FRUEH, Lisa; DODEAN, Rozalia; SMILKSTEIN, Martin; ALDAY, Holland; KOOP, Dennis; BLEYLE, Lisa; (43 pag.)WO2017/15360; (2017); 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 40546-94-9 as follows. Application In Synthesis of 6-Methyl-4-phenylchroman-2-one

Example 1[149] Preparation of 3-(2-methoxy-5-methylphenyl)-3-phenyl propionic acid; [150](H) (HI)[152] [153] A reaction mixture of 0.75 kg 3,4-dihydro-6-methyl-4-phenyl-2H-benzopyran-2-one, 0.262 kg sodium hydroxide and 0.93 L DM water was stirred at 55-65C for 2-3 hrs. The reaction was cooled to RT. 0.825 kg dimethylsulphate was added drop wise to reaction mixture within 1-2 hr. After the completion of addition, reaction mixture was stirred at same temperature for 1-2 hrs. Again solution of 0.186 kg sodium hydroxide in 0.93 L DM water was added at RT within 1 hr. The reaction mixture was stirred at 70-800C for 3-5 hrs. After completion of reaction, reaction was cooled to RT. 0.3 L Cone, hydrochloric acid was added drop wise to the reaction mixture till washing is neutral. The reaction mixture was stirred for 1-2 hrs, then filtered &; washed with 2.0 L DM water to obtain wet cake. The wet cake was dried at 55-600C for 10-12 hrs to obtain 3-(2-methoxy-5-methylphenyl)-3-phenyl propionic acid.[154] (Yield: 0.71 kg, 83%). [155] HPLC Purity: >; 95 %.

According to the analysis of related databases, 40546-94-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALEMBIC LIMITED; PONNAIAH, Ravi; DESAI, Sanjay; SHAH, Chankrakant Chunilal; PATEL, Kalpesh Shantibhai; PAREKH, Viral Maheshbhai; WO2010/92500; (2010); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 89-71-4, 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 89-71-4 as follows.

A mixture of methyl o-toluate (13.5 g, 89.9 mmol), NBS (17.6 g, 98.9 mmol), and benzoyl peroxide (50 mg, 0.2 mmol) in carbon tetrachloride (250 mL) was heated at reflux over the weekend. The reaction mixture was allowed to cool, and it was then filtered. The solvents were evaporated under reduced pressure and the residue was purified by chromatography, eluting with 3% ethyl acetate/hexanes to give 2-bromomethyl-benzoic acid methyl ester (7.7 g, 37%) as a white solid. 1HNMR (CDCl3): delta 7.97 (dd, J=1.5 Hz, 8.0 Hz, 1H), 7.49 (m, 2H), 7.38 (dt, J=1.5 Hz, 8.0 Hz, 1H), 4.96 (s, 2H), 3.94 (s, 3H). MS (APCI+): 231 (100), 229 (93).

According to the analysis of related databases, 89-71-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chu, Chang An; Gillespie, Paul; Tilley, Jefferson Wright; US2004/266856; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

79669-50-4, name is methyl 5-bromo-2-methyl-benzoate, 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. Computed Properties of C9H9BrO2

(2) A suspension of 1.19 g (9.46 mmol) of phenylboronic acid, 1.97 g (8.60 mmol) of methyl 5-bromo-2-methylbenzoate, 4 mg (0.017 mmol) of palladium (II) acetate, 2.97 g (21.5 mmol) of potassium carbonate, and 2.77 g (8.6 mmol) of tetrabutylammonium bromide in 20 ml of water was vigorously stirred under a stream of nitrogen, and stirred at 70 C. under an atmosphere of nitrogen for 1 hour. Water was added to the reaction mixture and it was extracted with tert-butyl methyl ether. The organic layer was dried and concentrated. The residue (1.9 g) was subjected to silica gel column chromatography (eluted with n-hexane:ethyl acetate=30:1) to obtain 1.65 g (7.29 mmol) of methyl 5-phenyl-2-methylbenzoate as an oil.

The synthetic route of 79669-50-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; US6489487; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, 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 816-27-3, name: Ethyl 2-ethoxy-2-iminoacetate

To a solution of cis-1-amino-3-[tert-butyl(dimethyl)silyl]oxy-5-phenyl-pyrrolidin-2-one (9.5 g, 31.0 mmol) in ethanol (250 mL) was added ethyl 2-ethoxy-2-imino-acetate (6.7 g, 46.5 mmol). The reaction mixture was stirred at 60 C. for 6 h and subsequently concentrated under reduced pressure to afford crude ethyl 2-[[cis-3-[tert-butyl(dimethyl)silyl]oxy-2-oxo-5-phenyl-pyrrolidin-1-yl]amino]-2-imino-acetate as a yellow oil (10.6 g, 84%), used in the next step without further purification. LCMS RT=2.106 min, m/z=406.2 [M+H]-. LCMS (10 to 80% acetonitrile in water+0.1% ammonia water over 3.0 mins) retention time 2.106 mm, ESI+ found [M+H]=406.2.

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-ethoxy-2-iminoacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Genentech, Inc.; Patel, Snahel; Hamilton, Gregory; (73 pag.)US2018/170927; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 3469-00-9, 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. 3469-00-9, name is Methyl Diphenylacetate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 4.2 General procedures: A. Microwave. Neat samples of amine (1.00 mmol) and carboxylic derivative (methyl ester or acid, 1.00 mmol) and DABAL-Me3 (202 mg, 0.8 equiv) were placed in a 5 mL microwave vial and dry THF added (1 mL) under a blanket of argon. For coupling partners containing acidic hydrogens additional DABAL-Me3 (total of 410 mg, 1.6 equiv) was used. The vial was promptly capped and placed in a CEM Discover microwave reactor. After irradiation (290 W, 130 C, 8 min) and programmed cool down (ca. 20 min). The reactions were quenched by cautious addition of HCl (2 M, 4 mL) or aqueous solutions of Rochelle salt (saturated potassium sodium tartrate, 4 mL) (CARE: methane liberated). Extraction with dichloromethane, drying (MgSO4) and evaporation frequently provided the pure products directly. If purification was required column chromatography 3:2 to 2:3 hexane:EtOAc was used for amides lacking highly polar functional groups (CH2Cl2 with 2 % v/v MeOH was used for amides bearing pendant amines, alcohols and other polar functional groups).

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

Reference:
Article; Dubois, Nathalie; Glynn, Daniel; McInally, Thomas; Rhodes, Barrie; Woodward, Simon; Irvine, Derek J.; Dodds, Chris; Tetrahedron; vol. 69; 46; (2013); p. 9890 – 9897;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 52787-14-1,Some common heterocyclic compound, 52787-14-1, name is Methyl 4-(2-methoxy-2-oxoethyl)benzoate, molecular formula is C11H12O4, 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 50-mE round-bottom flask was charged with methyl 4-(2-methoxy-2-oxoethyl) benzoate (1 g, 4.80 mmol), (dimethoxymethyl)dimethylamine (571 mg, 4.79 mmol) and N,N-dimethylformamide (15 mE). The resulting solution was stirred for 4 h at 60 C. Afier cooling to 23 C., the reaction was quenched with water (30 mE) and the product was extracted with ethyl acetate (3×30 mE). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by colunm chromatography eluting with ethyl acetate/petroleum ether (1:1 v/v) to afford methyl 4-(1 -(dimethylamino)-3- methoxy-3-oxoprop- 1 -en-2-yl)benzoate as a yellow solid (800 mg, 63%). ECMS: (ESI) mlz 264 [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 Methyl 4-(2-methoxy-2-oxoethyl)benzoate, its application will become more common.

Reference:
Patent; Forma Therapeutics, Inc.; Ioannidis, Stephanos; Talbot, Adam Charles; Follows, Bruce; Buckmelter, Alexandre Joseph; Wang, Minghua; Campbell, Ann-Marie; Schmidt, Darby Rye; Guerin, David Joseph; Caravella, Justin A.; Diebold, R. Bruce; Ericsson, Anna; Lancia, JR., David; (225 pag.)US2016/185785; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 41658-03-1, These common heterocyclic compound, 41658-03-1, name is Ethyl 3-bromopropiolate, 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: A dry and argon flushed Schlenk-flask, equipped with a magnetic stirring bar and a rubber septumwas charged with 1,8-bis(butylthio)-3,6-dichloro-2,7-naphthyridine (1.0 equiv) in THF. After cooling to-40 C, a solution of TMPLi (1 M in THF, 1.2 equiv) was slowly added. The reaction mixture wasstirred for 30 min at the same temperature. Then, the corresponding electrophile (1.2 equiv) wasadded and the solution was stirred at -40 C until complete conversion of the starting material(detected by GC-analysis of reaction aliquots).

The synthetic route of 41658-03-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Greiner, Robert; Blanc, Romain; Petermayer, Christian; Karaghiosoff, Konstantin; Knochel, Paul; Synlett; vol. 27; 2; (2016); p. 231 – 236;,
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 153559-48-9 as follows. Product Details of 153559-48-9

Example 3: Preparation of bexaroteneTo suspension of methyl 4-[l-(5,6,7,8-tetrahydro-3, 5,5,8, 8-pentamethyl-2-naphthalenyl)-l- ethenyljbenzoate (100 g) in methanol (1000 ml), 5N aqueous potassium hydroxide (170 ml) was added at 25-30C and the reaction mixture was refluxed for 8 hours. After completion of reaction (monitored by HPLC), reaction mass was cooled to 35-40 C and washed with 50% ethyl acetate: n-heptane mixture (2 x 500 ml). The organic layer was discarded and the aqueous layer was cooled to 10-15 C. Thereafter pH of aqueous layer was adjusted to 1-2 by addition of concentrated hydrochloric acid (100 ml). The resulting mixture was then stirred at 20-25C, stirred for 1 hour and precipitated solid was filtered. The resulting solid was slurry washed with demineralized water (100 ml), centrifuged and dried to give 84.6 g of title compound having purity 98.89 %, none of the impurities C, D, E, F were detected by HPLC

According to the analysis of related databases, 153559-48-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IND-SWIFT LABORATORIES LIMITED; BHIRUD, Shekhar, Bhaskar; SARIN, Gurdeep, Singh; SHARMA, Bimal, Kumar; GERA, Pardeep; WO2011/141928; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics