Category: 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., Formula: C5H10O4

Preparation of substituted 3-hydroxy isoquinolines were carried out in the manner described in Fukumi, H.; Kurihara, H.; Heterocycles., 1978, 9(9), 1197-1205. Thus, a mixture of 4-methyl benzylamine (5.54 g, 45.7 mmol) and methyl dimethoxyacetate (6.17 mL, 50.3 mmol) was heated to 130 C. where it stirred for 4 h. After this time, the volatiles were removed under reduced pressure to provide a residue. The residue was azeotroped to dryness from toluene to provide the product, which was used directly in the next step without further purification. MS (E+) m/z: 224 (MH+); LC retention time (Method A): 2.49 min.

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; Weinstein, David S.; Gilmore, John L.; Sheppeck, James; Yang, Bingwei Vera; Kim, Soong-Hoon; Vaccaro, Wayne; US2005/187242; (2005); A1;,
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Electric Literature of 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.

j00399j A mixture of(3,4-difluorophenyl) methanamine (2.0 g, 14 mmol) and methyl 2,2- dimethoxyacetate (3.8 g, 28 mmol) was stirred at 140 C for 1 hour in the microwave. On completion, the reaction mixture was diluted with dichloromethane (20 mL) and concentrated in vacuo to give cmde compound B-64 (4.3 g, crude) as a yellow solid. LCMS (E): tR=0.596 mi, (ES) mlz (M+H) =246.1.

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

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

Synthetic Route of 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.

The synthesis of {5-Bromo-l-[3-(methylsulfonyl)propyl]-lH-benzimidazol-2-yl}- methanol (fragment A2) was done as shown in scheme 6. refluxed overnightfragment A2Scheme 6 Compound 1 (7.6 g, 35 mmol), 3 -(methyl sulfonyl)propan-l -amine hydrochloride (6 g, 35 mmol) and diisopropylethylamine (DIEA) (13.5 g, 105 mmol) were dissolved in ethanol (70 mL) and refluxed for 14 h. The mixture was cooled to 20C. The precipitate was filtered and washed with ethanol. 11 g (94%) of compound 2 was obtained as an orange powder. Compound 2 (10 g, 29.7 mmol) in methanol (200 mL), EtOAc (200 mL) and THF (200 mL) was hydrogenated with Raney Ni (10 g) as a catalyst at 20C (1 atm) for 3h. After uptake of H2 (3 eq), the catalyst was filtered off and the filtrate was evaporated. 10 g (90%) of compound 3 was obtained as a black solid.Compound 3 (10 g, 29.7 mmol) and methyl dimethoxyacetate (9.2 g, 68.31 mmol) in 24 wt% KOEt in ethanol (13.5 g, 38.5 mmol) were stirred and refluxed overnight. The mixture was evaporated under vacuum. Water (200 mL) was added. Acetic acid was added to neutralize the mixture. The mixture was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with saturated NaHC03, brine and dried over Na2S04. The solvent was removed under vacuum to yield 12.3 g (90%) of compound 4 as dark oil. Compound 4 (12.3 g, 29.3 mmol) in THF (100 mL) was stirred for 0.5 h at 20C to dissolve. Cone. HCI (21 mL) and H20 (42 mL) were added.The mixture was refluxed for 6 h and then cooled to -10C. CH3OH (50 mL) were added, followed by careful addition of NaBH4 (24 g, 629 mmol). The mixture was stirred for 0.5 h at 10C and concentrated under vacuum. Water (200 mL) was added.The mixture was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine and dried over Na2S04. The solvent was removed under vacuum. The resulting solid was washed with ethyl acetate (2×5 mL) and dried under vacuum. 6.8 g (60%) of fragment A2 was obtained as an off-white solid, m/z = 347 & 349 (M+H)+Br pattern. 1H NMR (400 MHz, DMS0 ) delta ppm 2.20 (dq, J=7.8, 7.5 Hz, 2 H), 2.98 (s, 3 H), 3.16 – 3.24 (m, 2 H), 4.42 (t, J=7.4 Hz, 2 H), 4.73 (d, J=6.0 Hz, 2 H), 5.73 (t, J=5.8 Hz, 1 H), 7.42 (dd, J=8.7, 1.9 Hz, 1 H), 7.63 (d, J=8.5 Hz, 1 H), 7.79 – 7.83 (m, 1 H)

According to the analysis of related databases, 89-91-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN R&D IRELAND; COOYMANS, Ludwig Paul; DEMIN, Samuel Dominique; HU, Lili; JONCKERS, Tim Hugo Maria; RABOISSON, Pierre Jean-Marie Bernard; TAHRI, Abdellah; VENDEVILLE, Sandrine Marie Helene; WO2012/80446; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 89-91-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 89-91-8 name is Methyl 2,2-dimethoxyacetate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Lithium hexamethyldisilane (55 mL of a 1 .OM solution in tetrahydrofuran, 55mmoles) was added to a solution of 3-acetylpyridine (5.5 mL, 50 mmoles), methyl dimethoxy acetate (6.7 mL, 55 mmoles) and anhydrous tetrahydrofuran (100 mL) with cooling at -45 C. The resulting reaction mixture was allowed to warm to 25 C over 1 hour, and stirred at this temperature for 3 hours. The reaction mixture was then concentrated under reduced pressure, and the residue was suspended in methanol (50 mL) andconcentrated under reduced pressure. The resulting residue was suspended in methanol (150 mL) and treated with hydrazine monohydrate (2.62 mL, 55 mmoles) and glacial acetic acid (6.29 mL, 110 mmoles), and the reaction mixture was heated at reflux for 14 hours. The resulting reaction mixture was cooled to 25 C and concentrated under reduced pressure. The residue was partitioned between ethyl acetate (200 mL) and iN aqueous sodiumhydroxide solution (100 mL). The layers were separated, and the organic layer was washed successively with iN aqueous sodium hydroxide solution (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to yield 8.83 g of the title compound as a beige solid. 1H NMR (CDC13): oe 10.5 (br s, 1H) 9.03 (d, 1H), 8.57 (dd, 1H), 8.09 (dt, 1H), 7.34(dd, 1H), 6.65 (s, 1H), 5.63 (s, 1H), 3.39 (s, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2,2-dimethoxyacetate, and friends who are interested can also refer to it.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; CLARK, David, Alan; FRAGA, Breena, Gloriana; ZHANG, Wenming; WO2015/38503; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 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.

According to a general procedure for formation of a Weinreb intermediate,36 a vigorously stirred slurry of methyl dimethoxyacetate (4, 200 ^iL, 1.64 mmol) and N, O-dimethylhydroxylamine hydrochloride (201 mg, 2.05 mmol) in THF (2.4 mL) under argon was treated dropwise with isopropylmagnesium bromide (2.05 mL, 4.10 mmol, 2 M solution in THF) at -20 C. The resulting heterogeneous reaction mixture was stirred for 1.5 h at -20 C under argon. The reaction mixture was quenched with saturated aqueous NH4C1 and H20 (1 : 1). After extraction with ether (3 x 50 mL), the combined organic extract was washed (brine), dried (Na2S04) and concentrated under vacuum at room temperature. The ? NMR spectrum of the crude product showed unreacted 4 and signals consistent with those reported for l,l-dimethoxy-3-methylbutan-2-one (A).

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

Reference:
Patent; NORTH CAROLINA STATE UNIVERSITY; LINDSEY, Jonathan S.; MASS, Olga; WO2013/62670; (2013); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

89-91-8, name is Methyl 2,2-dimethoxyacetate, 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. name: Methyl 2,2-dimethoxyacetate

A mixture of 1-(2-bromophenyl)methanamine (4 g, 21.5 mmol) and methyl 2,2-dimethoxyacetate (3.60 g, 26.8 mmol) was stirred for 1 h at 80 C under nitrogen atmosphere. The mixture was cooled to room temperature and extracted with ethyl acetate (3*200 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with petroleum ether /ethyl acetate (1:1) to afford N-[(2-bromophenyl)methyl]-2,2-dimethoxyacetamide as a yellow solid (3 g, 48%). LCMS (ES, m/z): 288,290 [M+H]+.

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

Reference:
Patent; Forma Therapeutics, Inc.; Martin, Matthew W.; Zablocki, Mary-Margaret; Mente, Scot; Dinsmore, Christopher; Wang, Zhongguo; Zheng, Xiaozhang; (382 pag.)EP3636637; (2020); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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., Application In Synthesis of Methyl 2,2-dimethoxyacetate

Lithium hydroxide monohydrate (89.5 mmol, 3.75 g,1.2 equiv) was added at 0 C to a solution of methyl dimethoxyacetate (74.6 mmol, 10 g, 1 equiv) in dioxane (45 mL) and water (45 mL). The mixture was stirred for 1 h at 0 C and one additional hour at room temperature. Sodium hydroxide (1M aq soln, 75 mL) was subsequently added and the mixture extracted with diethyl ether (3 x 75 mL). The recovered aqueous layer was acidified with hydrogen chloride (6N aq soln) until a pH of 1-2 then the organics extracted with diethyl ether (3 x 75 mL). The combined organic layers were subsequently dried with magnesium sulfate, filtrated and the solvent slowly evaporated under reduced pressure to conduct to the desired carboxylic acid in a quantitative yield. Colorless liquid; Yield: 99%

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; Munyemana, Francois; George, Isabelle; Devos, Alain; Colens, Alain; Badarau, Eduard; Frisque-Hesbain, Anne-Marie; Loudet, Aurore; Differding, Edmond; Damien, Jean-Marie; Remion, Jeanine; Van Uytbergen, Jacqueline; Ghosez, Leon; Tetrahedron; vol. 72; 3; (2016); p. 420 – 430;,
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., HPLC of Formula: C5H10O4

12. 55 g (0.094 mol) of methyl 2, 2-dimethoxyacetate and12 g (0.24 mol) of hydrazine hydrate were mixed in a 100 mL round-bottomed flask and heated to 100 C and maintained at 100 C for 5 h, after which the temperature was slowly heated to 160 C over 4 h (15 C) The excess hydrazine hydrate and water produced during the reaction were removed and maintained at 160 C for 10 h. The column was cooled (the volume ratio of the eluent used was ethyl acetate: petroleum ether = 4: 1) 4-amino-3,5-dimethoxymethyl-4-yl-1,2,4-triazole (11) 9.88 was obtained in 45% yield. Melting point: 71-74 (:. The reaction of dimethoxy acetic acid methyl ester and hydrazine hydrate molar ratio is 1: 2.5;

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 89-91-8.

Reference:
Patent; Tianjin Normal University; Tian, Li; Shang, Zhou; Yong, Li Xin; (13 pag.)CN103980256; (2016); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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., COA of Formula: C5H10O4

j00477j A mixture of (3 -chloro-4-fluorophenyl)methanamine (2.0 g, 13 mmol) and methyl 2,2- dimethoxyacetate (1.7 g, 13 mmol) was stirred at 140 C for 1 hour in microwave. On completion, the mixture was concentrated in vacuo to give compound B-103 (3.3 g, cmde) as a yellow gum. LCMS (B): tR = 0.711 mm., (ES) mz (M+H) + = 262.2.

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; 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

Synthetic Route of 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.

Step F; 5-Bromo-6-ethyl-N*2*-isopropyl-pyridine-2, 3-diamine (1 g) is dissolved in diethoxymethylacetate (4 mL) and is heated at 120 C for 90 min. After cooling to RT the mixture is directly purified by flash column chromatography on silica gel to give 6-bromo-5- ETHYL-3-ISOPROPYL-3H-IMIDAZO [4,5-b] pyridine as colorless oil. Rf (hexane: EtOAc = 2: 1) = 0.32

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

Reference:
Patent; NEUROGEN CORPORATION; AVENTIS PHARMACEUTICALS INC.; WO2005/23806; (2005); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics