Category: 89-91-8

Some common heterocyclic compound, 89-91-8, name is Methyl 2,2-dimethoxyacetate, molecular formula is C5H10O4, 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. 89-91-8

To a solution of methyl 2,2-dimethoxyacetate (8.7 g, 64.9 mmol, 7.98 mL, 1 eq) in dioxane (50 mL) and H20 (50 mL) was added LiOH H20 (3.27 g, 77.8 mmol, 1.2 eq) at 0 C . After addition, the mixture was stirred at this temperature for 1 h, and then the resulting mixture was stirred at 20C for 10 h. TLC indicated that one new spot formed. The reaction mixture was diluted with NaOH aqueous solution (1 M, 80 mL), and extracted with petroleum ether (80 mL x 3). The combined aqueous layers were acidified with HC1 (6 M) aqueous solution to pH=l, and then extracted with ethyl acetate (80 mL for 3 times). The combined organic layers were dried over Na2S04, filtered and concentrated under reduced pressure to give 3.54 g of a colorless oil, which was used directly in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 89-91-8, its application will become more common.

Reference:
Patent; SIGILON THERAPEUTICS, INC.; VEISEH, Omid; HEIDEBRECHT, Richard; WOTTON, Paul, Kevin; OBERLI, Matthias; MILLER, Robert, James; (498 pag.)WO2018/67615; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

89-91-8, 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. 89-91-8, name is Methyl 2,2-dimethoxyacetate, A new synthetic method of this compound is introduced below.

Step 1 : Preparation of 1-(2,4-dichloropyridin-3-yl)-2,2-dimethoxyethan-1-one . A cold (-78 C) solution of 2,4-dichloro-3-iodopyridine (2.73 g, 9.968 mmol) in THF (49.84 mL) was treated dropwise with 2.5 M n-BuLi in hexanes (4.785 mL, 11.96 mmol). After stirring for 20 min at -78 C, the reaction mixture was treated dropwise with methyl 2,2-dimethoxyacetate (1.708 mL, 13.95 mmol). The resulting mixture was stirred for 1 h at -78 C, before quenching with saturated NH4Cl(aq) (10 mL). The quenched mixture was allowed to warm to ambient temperature. Subsequently, the mixture was diluted with water (30 mL), and extracted with EtOAc. The organic extracts were dried over anhydrous Na2S04(S>, filtered, and concentrated in vacuo. The crude residue was purified by silica chromatography (0-30% EtOAc in hexanes) to afford the title compound (1.9 g, 76%).

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; ARRAY BIOPHARMA INC.; WALLS, Shane M.; REN, Li; RAMANN, Ginelle A.; MORENO, David A.; METCALF, Andrew T.; MCFADDIN, Elizabeth A.; KOLAKOWSKI, Gabrielle R.; BLAKE, James F.; DAI, Donghua; HAAS, Julia; JIANG, Yutong; KAHN, Dean; (368 pag.)WO2019/143994; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

89-91-8, 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 89-91-8 as follows.

j00471j A mixture of(4-chloro-3-fluorophenyl)methanamine (2.0 g, 12.5 mmol) and methyl 2,2- dimethoxyacetate (3.4 g, 25.1 mmol) was stirred at 140 C for 1 hour in microwave. On completion, the reaction was diluted with dichloromethane (200 mL) and concentrated under reduced pressure togive compound B-100 (4.9 g, crude) as a yellow gum. LCMS (B): tR = 0.665 mm., (ES) mlz (M+H)=262.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 89-91-8, and friends who are interested can also refer to it.

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); 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. 89-91-8, name is Methyl 2,2-dimethoxyacetate, This compound has unique chemical properties. The synthetic route is as follows., 89-91-8

General procedure: To a solution of diisopropylamine (1.5 eq.) in THF (1.5M) at ooc under N2 was added nBuli(1.4eq., 1.6M in hexane) and the mixture was stirred for 20 min. The LOA was cooled to -80C20 and TMSCI (1.4 eq.) was added followed by the methyl ester (1 eq.). The reaction was allowedto reach ooc over 3 h, brought to rt and stirred for 30 min. Pentane was added and the whiteprecipitate filtered off over celite. The solvent was removed under reduced pressure. Purificationif necessary was performed by bulb-to-bulb distillation.

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; SANDOZ AG; HOEFERL-PRANTZ, Kathrin; FELZMANN, Wolfgang; WILHELM, Thorsten; BENITO-GARAGORRI, David; WO2013/189980; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 89-91-8, name is Methyl 2,2-dimethoxyacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 89-91-8

Method 1; Ethyl 4,4-dimethoxy-3 -oxobutanoate; To a solution of dimethoxy methyl acetate (25 g, 0.19 mol) in EtOAc (75 ml), was added sodium hydride (8.5 g, 0.21 mol) in portions. After all the sodium hydride was added, the mixture was set to reflux for 10 hours. The reaction mixture was poured onto cold water followed by pH adjustment to 3-4 using 3N HC1 solution. The layers were separated and the organic layer was dried, filtered, and concentrated in vacuo to afford 34 g (96% crude recovery) of the title compound, which was used further without purification.

The synthetic route of 89-91-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/8523; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics