Tag: M.W=100-200

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., Safety of Methyl 2,2-dimethoxyacetate

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;,
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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. 4385-35-7, name is 3-Isochromanone belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H8O2

To a suspension of isochromanone (99% pure, 149.7 g, 1.00 mol) in methanol (280 mL) was added dropwise over a period of 90 min at 14-16 C. sodium methanolate (30% in methanol, 270.0 g, 1.50 mol) and the resulting mixture was stirred for 90 min at 15 C. To this mixture was added dropwise over a period of 6.5 h at 9-13 C. iso-butyl nitrite (94% pure, 137.1 g, 1.25 mol) and the mixture was stirred at 8 C. overnight. The conversion was monitored by HPLC. After completion of the reaction, 4 M hydrochloric acid was added to adjust a pH<1 before the resulting suspension was stirred for overnight at 4 C. The crude product was collected by filtration, washed with cold dist. water (2×500 mL) and dried in vacuo at max. 45 C. Isochroman-3,4-dione-4-oxime was obtained as a colorless solid (145.9 g, 90.4 HPLC-area %, 74% yield).1H-NMR (DMSO-d6): delta=13.3 (s, 1H), 8.34 (d, J=7.4 Hz, 1H), 7.54-7.41 (m, 3H), 5.46 (s, 2H) ppm; 13C-NMR (DMSO-d6): delta=162.3, 140.2, 133.2, 130.2, 129.0, 127.9, 125.4, 125.0, 68.3 ppm; mp=179-182 C. The synthetic route of 4385-35-7 has been constantly updated, and we look forward to future research findings. Reference:
Patent; BASE SE; US2011/295022; (2011); 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. 105-53-3, name is Diethyl malonate, A new synthetic method of this compound is introduced below., COA of Formula: C7H12O4

(a) Isobutyldiethyl malonate Diethyl malonate is treated with an ethanol and sodium ethoxide mixture. Then iso-butyl bromide is added to form isobutyl diethyl malonate as the product of this malonic ester synthesis.

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; E. R. Squibb & Sons, Inc.; US4382081; (1983); A;,
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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. 1195768-18-3 name is Methyl 3-amino-2-fluorobenzoate, 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. 1195768-18-3

A 500 mL round-bottomed flask was charged with methyl 3-amino-2- fluorobenzoate (20 g, 1 18 mmol) and pyridine (10.52 mL, 130 mmol) in dichloromethane (DCM) (100 mL) to give a yellow/clear solution at 0 C. After 5 min, 1 -propanesulfonyl chloride (13.26 mL, 1 18 mmol) was added to the reaction and warmed to room temperature. After 24 h, the reaction mixture was diluted with EtOAc (200 mL) and concentrated to a volume of 50 mL. The reaction mixture was diluted with EtOAc (200 mL) and water (200 mL) and stirred. After stirring, the EtOAc layer was separated from the water layer. The EtOAc layer was diluted with water (200 mL). After stirring, the EtOAc layer was separated from the water layer. The EtOAc layer was dried over Na2SO4, filtered, and concentrated to 50 mL. While stirring, the reaction mixture was diluted with EtOAc (50 mL) and hexanes (200 mL) and stirred. The solids were filtered and washed with hexanes. The product was put into drying oven for 1 day to obtain methyl 2-fluoro-3- [(propylsulfonyl)amino]benzoate. 28.9 g (105 mmol, 89 % yield) MS: 276 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-2-fluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE LLC; ADAMS, Jerry, Leroy; FAITG, Thomas; KASPAREC, Jiri; PENG, Xin; RALPH, Jeffrey; RHEAULT, Tara Renae; WATERSON, Alex Gregory; WO2011/59610; (2011); A1;,
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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. 18595-14-7, name is Methyl 4-amino-3-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H11NO2

TEA (1.2 mmol) and the commercially available benzoyl chloride (1.1 mmol) wereadded at 000 to a solution of the corresponding aniline (1 mmol) in DCM (0.16M). The reaction mixture was left stirring at room temperature for 2h. Sat. solution of NaHCO3 (500m1) was added. The phases were separated and the aqueous layer was extracted with DCM (3 times). The combined organic layers were evaporated and purified by flash chromatography eluting with DCM/EtOAc to obtain the compounds of examples16-18,20,21 reported in Table 4.

The synthetic route of 18595-14-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROTTAPHARM BIOTECH S.R.L.; ARTUSI, Roberto; CASELLI, Gianfranco; ROVATI, Lucio; (78 pag.)WO2016/146220; (2016); A1;,
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Reference 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;,
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Synthetic Route of 39552-81-3, 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 39552-81-3 as follows.

EXAMPLE 3 N-(4-Methoxycarbonylmethylphenyl)-L-glutamine: Compound (3) Following the procedure described in (a) of Example 1, 11.14 g (0.03 mole) of N-carbobenzoxy-L-glutamic acid alpha-benzyl ester was reacted with 4.96 g (0.03 mole) of methyl p-aminophenylacetate to give 13.38 g (88% yield) of an intermediate. The intermediate was dissolved in 500 ml of tetrahydrofuran, 200 ml of methanol and 100 ml of water. To the solution was added 0.5 g of palladium black and the mixture was subjected to hydrogenation at atmospheric pressure to give 6.09 g (79% yield) of N-(4-methoxycarbonylmethylphenyl)-L-glutamine, m.p. 183.3-184.2 C. [alpha]D25 =+29.2 (c=1 2 N HCl)

According to the analysis of related databases, 39552-81-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Chemical Industries Ltd.; Nippon Shinyaku Co., Ltd.; US4439448; (1984); A;,
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Some common heterocyclic compound, 14920-81-1, name is Methyl 2,6-dimethylbenzoate, molecular formula is C10H12O2, 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. Formula: C10H12O2

General procedure: To a flame-dried 250 mL round-bottom flask under argon wereadded 4 (8.02 g, 28.4 mmol, 1 equiv), TMEDA (8.71 mL, 58.2mmol, 2.05 equiv), and anhydrous n-hexane (28 mL). Theresulting solution was cooled in an ice bath and sec-butyllithium(1.4 M solution in cyclohexane, 42.0 mL, 58.2 mmol, 2.05equiv) was added dropwise. The ice bath was removed and thereaction mixture was stirred at room temperature for 4 h. Thereaction was cooled to -78 C and a solution of methyl 2,4,6-trimethylbenzoate (5.11 g, 28.7 mmol, 1.01 equiv) in anhydrousn-hexane (28 mL) was added slowly via cannula. After the addition,the mixture was allowed to slowly warm to room temperatureand stirred for 12 h. The reaction was quenched with water(25 mL) and the biphasic mixture was stirred vigorously for 30min. The mixture was diluted with Et2O (100 mL) and the layerswere separated. The organic layer was washed with water(2 × 150 mL) and brine (1 × 150 mL). The organic layer wastransferred to a 250 mL round-bottom flask equipped with astir bar. To the vigorously stirred solution was added conc. HCl(12 mL), resulting in a bright-yellow precipitate. The suspensionwas stirred vigorously for 30 min then diluted with water (150mL). The layers were separated and the organic layer wasextracted with water (3 × 150 mL or until the washings becomecolorless). To the combined aqueous layers was added solidNaBF4 (9.35 g, 85.2 mmol, 3 equiv), resulting in a bright-yellowprecipitate. The resulting suspension was extracted withdichloromethane (3 × 150 mL or until the washings become colorless).To the combined organic layers was added HBF4·Et2Ocomplex (3.46 mL, 28.4 mmol, 1 equiv). The solution wasswirled to achieve homogeneity then washed with water(1 × 100 mL) and aq. NaBF4 (1 M, 1 × 100 mL). The organic layerwas dried over solid NaBF4, filtered, and concentrated to dryness.The residue was purified by trituration with hexanes andfiltered. The solid was rinsed with n-pentane and dried in vacuoto give xanthylium 3 (10.6 g, 21.3 mmol, 75% yield) as a yelloworangesolid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 14920-81-1, its application will become more common.

Reference:
Article; White, Alexander R.; Wang, Leifeng; Nicewicz, David A.; Synlett; vol. 30; 7; (2019); p. 827 – 832;,
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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 2967-93-3 as follows. category: esters-buliding-blocks

Step 2; Preparation of 2-Fluoro-5-formyl-benzoic acid methyl ester; Add Af-bromosuccinimide (2.46 g, 13.86 mmol) and benzoyl peroxide (0.152 g, 0.630mmol) to a solution of 2-fluoro-5-methyl-benzoic acid methyl ester (1.06 g, 6.30 mmol)in carbon tetrachloride (50 mL). Heat the mixture at reflux for 4 h. Cool the mixture toroom temperature and wash with saturated aqueous sodium bicarbonate solution (10 mL)and brine (10 mL). Dry the organic layer over anhydrous sodium sulfate, filter, andconcentrate under reduced pressure. Dissolve the resulting residue in dimethylsulfoxide(30 mL) and heat at reflux for 16 h. Cool the mixture to room temperature and dilutewith water (100 mL) and ethyl acetate (100 mL). Extract the aqueous layer with ethylacetate (3 x 100 mL). Wash the combined organic layers with water (3 x 100 mL),followed by brine (100 mL). Dry the organic layer over anhydrous sodium sulfate, filterand concentrate. Purify the residue by chromatography over silica gel, eluting withhexanes/ethyl acetate (80:20), to provide the title compound as a tan solid (0.228 g, 20%).

According to the analysis of related databases, 2967-93-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/2342; (2006); 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. 61644-18-6, name is Chloromethyl isobutyrate, A new synthetic method of this compound is introduced below., Recommanded Product: 61644-18-6

General procedure: To a solution of Compound 54B (150 mg, 0.24 mmol) in DMF (10 mL) was added chloromethyl isobutyrate (36 mg, 0.24 mmol) and Na2CO3 (50 mg, 0.48 mmol). The reaction mixture was stirred at 50 C for 3 hour. After cooling down to room temperature, the mixture was diluted with water (50 mL) and extracted with ethyl acetate (20 mL x 3). The combined extracts were washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to furnish Compound 54C. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used.

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; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
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Ester – an overview | ScienceDirect Topics