Category: 89-91-8

Application of 89-91-8, These common heterocyclic compound, 89-91-8, name is Methyl 2,2-dimethoxyacetate, 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.

Methyl dimethoxyacetate (19.9 g, 148 mmol) and compound C2 (15.6 g, 74.2 mmol) were combined with molecular sieves (16 g), and the mixture was treated with a solution of potassium t-butoxide in THF (1.0M, 150 mL, 150 mmol). The reaction mixture was heated to reflux for about 18 h; it was then filtered, and the collected solid was rinsed with additional THF. The combined filtrates were neutralized with acetic acid and concentrated in vacuo. The residue was purified by silica gel chromatography (Eluant: 5% MeOH in chloroform) to afford C10 as a white solid. Yield: 9.8 g, 33 mmol, 44%. MS (APCI) m/z 295.2 (M+1). 1H NMR (300 MHz, CDCl3) delta 1.91 (br d, J=10.5 Hz, 2H), 2.38 (m, 2H), 3.48 (s, 6H), 3.60 (dd, J=11, 12, 2H), 4.14 (br d, J=11 Hz, 2H), 4.90 (m, 1H), 5.22 (s, 1H), 8.10 (s, 1H), 9.52 (br s, 1H).

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

Reference:
Patent; Pfizer Inc.; US2010/190771; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application 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.

STR12 A mixture of methyl dimethoxyacetate (1) (8 mL, 65.5 mmol), glyoxylic acid monohydrate (5.8 g, 63 mmol) and p-toluenesulfonic acid monohydrate (60 mg, 0.32 mmol) was heated at 80 C. for 18 h. The resulting solution was cooled to 0 C. and phosphorus pentoxide (7.0 g, 49.3 mmol) was added. After heating for 4 h at 80 C., methyl glyoxylate (2) (7.9 g, 90 mmol) was obtained by distillation in 70% yield.

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; Akzo Nobel, N.V.; US6150548; (2000); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application 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.

To a solution of 2-chlorobenzylamine (30.0 g, 212 mmol) in MeOH (200 mL) was added triethylamine (36.7 mL, 265 mmol) and methyl dimethoxyacetate (31.0 g, 233 mmol). The reaction was heated to 80 C for 20 h. After cooling to room temperature, the reaction wasconcentrated in vacuo. EtOAc (300 ml) was added, washed with iN HC1 (300 mL x 2) and sat. aq. NaHCO3 (300 mL x 2). The organic layer was dried over anhydrous Na2SO4, filtered andconcentrated in vacuo to give the title compound (40.0 g, crude) as colorless oil that required no further purification. ?H NMR (400 IVIFIz, CDC13) 7.39 – 7.33 (m, 2H), 7.24 – 7.21 (m, 2H),4.73 (s, 1H), 4.56 (d, J 6.0 Hz, 2H), 3.38 (s, 6H).

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; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy M.; WAI, John; LAI, Kwong Wah; WANG, Fei; CHEN, Kevin X.; (351 pag.)WO2017/205538; (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., SDS of cas: 89-91-8

A diethyl ether solution of ethylmagnesium bromide (concentration=2 1.85 mass %, 277 g) was added to a reaction flask and was cooled to around 0 C. by stirring on an ice-cooling bath. A Grignard reaction was carried out by the dropwise addition to this solution over one hour of methyl dimethoxyacetate (25 g). This was followed by return to room temperature and reaction for 12 hours. The reaction solution was ice-cooled; 200 g of a saturated aqueous ammonium chloride solution was added dropwise; and the pH was subsequently adjusted to around neutrality by the dropwise addition of 10 mE of a 36% hydrochloric acid solution. The solution was then transferred to a separatory funnel; the organics were extracted with 50 g of hexane and separated; and drying was carried out over an appropriate amount of magnesium sulfate. This hexane suspension was filtered followed by removal of the solvent on an oil bath at around 65 C. Distillation was performed under reduced pressure on an oil bath at around 100 C. to obtain 22.4 g of a transparent and colorless 3-dimethoxym- ethyl-3-pentanol (GC purity=96.3%). 10 g of pure water and 1 g of 36% hydrochloric acid were added under ice cooling to 7 g of the 3-dimethoxymethyl-3-pentanol and stirring was carried out overnight. After this, 9.5 g of a 33% aqueous ethylamine solution was added dropwise under ice cooling and a reaction was run for 10 hours. The pH of the reaction solution at this time was 10 to 11. When stirring was stopped, separation occurred into an aqueous layer and a small amount of an organic layer, and the organic layer was determined to be alcohol compound No. 140 according to the NMR results. 2.7 g of the target was obtained for a yield of 33%.

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; ADEKA CORPORATION; SAKURAI, Atsushi; HATASE, Masako; YOSHINO, Tomoharu; ENZU, Masaki; (40 pag.)US2017/129912; (2017); 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

EXAMPLE 6 2,2-Dimethoxy-N-(3,4-dimethoxybenzyl)-acetamide 16.7 g. (0.1 mole) 3,4-dimethoxybenzylamine are contacted with 13.4 g. (0.1 mole) methyl 2,2-dimethoxyacetate for 3 hours. The reaction mass solidifies. The crude product is recrystallized from about 1 liter of a light petroleum ether fraction to give 19.4 g. of 2,2-dimethoxy-N-(3,4-dimethoxybenzyl)-acetamide in the form of white needles. A sample intended for analysis is sublimed at 70 C./0.03 mm.Hg. The yield is 72% of theory. The product has a melting point of 60 C. Infrared spectroscopy (CCl4) (cm-1): 3440 (NH), 2950 (CH3), 2850 (OCH3), 1680 + 1510 (CONH), 1600, 1460, 1115 + 1070 (CO) NMR (CDCl3): 6.84 (4H, singlet, Ha); 4.72 (1H, singlet, Hb); 4.38 (2H, doublet, Hc, J=6Hz); 3.87 (6H, singlet, Hd); 3.39 (6H, singlet, He) STR11 Mass spectrum: m/e 269 (M+), 237 (–CH3 OH), 222, 206 (M* at 209), 181, 166 (amine), 151 (tropylium), 75, 47, 31 (M* at 29.5) Analysis: C13 H19 NO5 (M.W. 269.3): calculated: C 57.98%; H 7.11%; N 5.20%; found: 57.95%; 7.15%; 5.17%

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

Reference:
Patent; U C B, Societe Anonyme; US4041077; (1977); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 89-91-8, name is Methyl 2,2-dimethoxyacetate, 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 89-91-8, name: Methyl 2,2-dimethoxyacetate

Compound 7 (15mmol) and methyl 2,2-dimethoxypropionate (30mmol) were kept in a 10mL screw-capped vial was stirred at 80C overnight. The reaction mixture was loaded on silica and resulting 110 dimethoxy acetamide intermediate 8 was purified by silica column chromatography using hexane and ethylacetate at a ratio of 2:1. The resulted compound without further purification was dissolved in 5mL concentrated sulfuric acid and stirred at 40C overnight. Subsequently, the acidic solution poured into ice-water, and the precipitate was collected and washed with water and diluted sodium bicarbonate solution [16]. The yield was 42%.1H NMR (500MHz, DMSO-d6) delta 8.91 (s, 1H, H1-isoquinoline), 7.64 (d, J=8.4Hz, 1H), 7.49 (d, J=8.4Hz, 1H), 6.87 (s, 1H, H4-isoquinoline), 5.74 (bs, 1H, OH), 2.54 (s, 3H, CH3).

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:
Article; Assadieskandar, Amir; Yu, Caiqun; Maisonneuve, Pierre; Liu, Xu; Chen, Ying-Chu; Prakash, G.K. Surya; Kurinov, Igor; Sicheri, Frank; Zhang, Chao; European Journal of Medicinal Chemistry; vol. 146; (2018); p. 519 – 528;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 89-91-8, 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.

Intermediate 55a: heptyl 2,2-bis(heptyloxy)acetate To a solution of methyl 2,2-dimethoxyacetate (5.0g, 37.3 mmol) in heptanol (26.3 ml_, 186 mmol) was added camphorsulfonic acid (0.43g, 1.86 mmol), and the reaction was heated to 100 C, overnight. The reaction was cooled to ambient temperature and concentrated under reduced pressure. The concentrate was purified on silica gel with dichloromethane / heptane as eluent to provide 4.0g of the desired compound. 1H NMR (400 MHz, CDCI3): delta = 4.86 (s, 1 H), 4.21 (t, J = 6.78 Hz, 2H), 3.52-3.69 (m, 4H), 1.55-1.77 (m, 6H), 1.20-1.45 (m, 24H), 0.82- 0.98 (m, 9H) ppm.

The chemical industry reduces the impact on the environment during synthesis Methyl 2,2-dimethoxyacetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; BRITO, Luis; CHEN, Delai; GAMBER, Gabriel Grant; GEALL, Andrew; LOVE, Kevin; ZABAWA, Thomas; ZECRI, Frederic; WO2015/95346; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 89-91-8, name is Methyl 2,2-dimethoxyacetate, 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: 89-91-8

Cyclohexanone Compound 2a (1.37 g, 14.0 mMol) in THF (5 mL) was added dropwise to a solution of LHMDS (16.0 mL, 16.0 mMol) in anhydrous THF (25 mL) at -78 C. under a N2 atmosphere. The solution was stirred at -78 C. for about 1 hr. Methyl dimethoxyacetate Compound 11a (1.88 g, 14.0 mMol) in anhydrous THF (5 mL) was then added dropwise. The reaction mixture was stirred while warming to r.t. over a period of about 15 hrs, then the reaction was quenched with water (5 mL). The organic layer was diluted with EtOAc (100 mL) and washed with water and brine. The organic layer was separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude product as an oil. The oil was purified by flash chromatography (eluted with 10% EtOAc in hexane) to afford 2-(2,2-dimethoxy-acetyl)-cyclohexanone Compound 11b (1.82 g, 65%). Benzylhydrazine dihydrochloride Compound 11c (1.75 g, 9.00 mMol) and K2CO3 (1.51 g, 10.92 mMol) were added to a solution of Compound 11b (1.80 g, 9.10 mMol) in MeOH (50 mL) at 0 C. under a N2 atmosphere. The reaction mixture was stirred overnight while warming to r.t., then the reaction was quenched with water (20 mL). The organic layer was diluted with EtOAc (200 mL) and washed with water and brine. The organic layer was separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude product as an oil. The oil was purified by flash chromatography (eluted with 20% EtOAc in hexane) to afford 1-benzyl-3-dimethoxymethyl-4,5,6,7-tetrahydro-1H-indazole Compound 11d (1.80 g, 70%) as a colorless oil. 3N HCl (8 mL) was added to a solution of Compound 11d (1.70 g, 5.9 mMol) in acetone (50 mL) at 0 C. under a N2 atmosphere. The reaction mixture was stirred for 4 hrs while warming to r.t., then the reaction was quenched with water (20 mL), neutralized to pH 7 with K2CO3 and diluted with CH2Cl2 (100 mL). The organic layer was washed with water and brine, separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to afford a 1-benzyl-4,5,6,7-tetrahydro-1H-indazole-3-carbaldehyde Compound 11e (1.35 g, 95%) as a colorless oil. Methanesulfonyl chloride Compound 11f1 (2.0 g, 17 mMol) and TEA (2.43 mL, 17.46 mMol) were added to a solution of (1R)-1-phenyl-ethylamine Compound 11f2 (1.75 g, 17.5 mMol) in CH2Cl2 (50 mL) at 0 C. under a N2 atmosphere. The mixture was stirred for 3 hrs while warming to r.t., then the reaction was quenched with water (5 mL). The organic layer was diluted with CH2Cl2 (100 mL) and then washed with water and brine. The organic layer was separated, dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to afford the corresponding N-(1-phenyl-ethyl)-methanesulfonamide Compound 11f3 as an oil. (Boc)2O (di-tert-butyldicarbonate) (4.57 g, 21.0 mMol) and DMAP (8 mg) were added to a solution of the methanesulfonamide Compound 11f3 in CH2Cl2 (10 mL) at 0 C. under a N2 atmosphere. The mixture was stirred overnight while warming to r.t., then the reaction was quenched with a saturated solution of NaHCO3 (sodium bicarbonate) (10 mL). The organic layer was diluted with CH2Cl2 (100 mL) and then washed with water and brine. The organic layer was separated, dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude Boc-protected methanesulfonamide product. The product was purified by flash chromatography (eluted with 10% EtOAc in hexane) to afford (methylsulfonyl)[(1R)-1-phenyl-ethyl]-carbamic acid tert-butyl ester Compound 11f (3.89 g, 80%) as a colorless oil. Adapting a published procedure (Tozer M J, Woolford A J A and Linney I A, Synlett, 1998, 2, 186-188) to obtain the target compound, a 1M solution of KOtBu (potassium tert-butoxide) in THF (0.75 mL, 0.75 mMol) was added dropwise to a solution of the ester Compound 11f (0.070 g, 0.250 mMol) in anhydrous THF (5 mL) at -78 C. under a N2 atmosphere. After 45 min, Compound 11e (0.060 g, 0.250 mMol) diluted in THF (3 mL) was added dropwise. The solution was reacted over a 15 hr period while warming to ambient temperature. The reaction was quenched with water (5 mL). The organic layer was diluted with EtOAc (100 mL) and then washed with water and brine. The organic layer was separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude product. The product was purified by flash chromatography (eluted with 20% EtOAc in hexane) to give Compound 260 (0.079 g (75%), as a white solid. MS m/z 422 (MH+); 1H NMR (CDCl3, 400 MHz) delta 7.56 (d, J=15.5 Hz, 11H), 7.35-7.19 (m, 8H), 7.11-7.09 (m, 2H), 6.42 (d,J=15.5 Hz, 1H), 5.21 (s, 2H), 4.61-4.11 (m, 2H), 2.45-2.41 (m, 2H), 2.36-2.33 (m, 2H), 1.75-1.67 (m, 4H), 1.55 (d, J=6.5 Hz, 3H).

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

Reference:
Patent; Lagu, Bharat; Liotta, Fina; Pan, Meng; Wachter, Michael P.; Xia, Mingde Xia; US2005/228034; (2005); 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.

To a solution of lithium aluminium hydride (3.4 g) in tetrahydrofuran (150 mL) was added dropwise a solution of methyl dimethoxyacetate (9.83 mL) in tetrahydrofuran (50 mL) under ice-cooling, and the mixture was stirred at 0 C. for 3 hr. To the reaction mixture was added sodium sulfate decahydrate (45 g) at 0 C., and the mixture was filtered through Celite. The solvent was evaporated under reduced pressure to give the title compound (5.45 g). 1H NMR (300 MHz, DMSO-d6) delta 3.27 (6H, s), 3.32-3.37 (2H, m), 4.29 (1H, t, J=5.5 Hz), 4.69 (1H, t, J=6.1 Hz).

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KAMEI, Taku; ARIKAWA, Yasuyoshi; OHASHI, Tomohiro; IMAEDA, Toshihiro; FUJIMORI, Ikuo; MIKI, Takashi; YONEMORI, Jinichi; OGURO, Yuya; SUGIMOTO, Takahiro; SETO, Masaki; NISHIDA, Goushi; KAMATA, Makoto; IMOTO, Hiroshi; (132 pag.)US2018/155333; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 89-91-8, These common heterocyclic compound, 89-91-8, name is Methyl 2,2-dimethoxyacetate, 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 mixture of the appropriate nitrile (4, 2 mmol), hydroxylamine50% (0.132 g, 2 mmol), and a catalytic amount of AcOH was stirredat 150 C for 40 min. After nearly complete conversion to thecorresponding amidoxime, as was indicated by TLC monitoring, theappropriate 2,2-dialkoxyacetate (6, 2 mmol) and K2CO3 (0.276 g,2 mmol) were added to the reaction mixture which was stirred at100 C for further 6 h. After completion of the reaction as indicatedby TLC, the reaction mixture was cooled to room temperature andthe residue was purified by column chromatography using n-hexane-EtOAc (6:1) as eluent. The solvent was removed, and the product was obtained.

Statistics shows that Methyl 2,2-dimethoxyacetate is playing an increasingly important role. we look forward to future research findings about 89-91-8.

Reference:
Article; Adib, Mehdi; Saeedi, Sara; Soheilizad, Mehdi; Bayanati, Maryam; Tajbakhsh, Mahmood; Amanlou, Massoud; Journal of Chemical Research; vol. 40; 5; (2016); p. 314 – 317;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics