Tag: M.W=100-200

Application of 61644-18-6, A common heterocyclic compound, 61644-18-6, name is Chloromethyl isobutyrate, molecular formula is C5H9ClO2, 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: Carboxylic acid (±)-9 (5.18 mmol) was dissolved in N,N-dimethylformamide (15.5 mL). Cesium carbonate (4.14 mmol) was added to the solution and the suspension was stirred during 2-3 min after which chloromethyl 2-methylpropanoate (6.73 mmol) was added. After stirring at room temperature during 18-24 h, dichloromethane (30 mL) was added to the mixture and the resulting organic phase was successively washed with water (3×20 mL) and brine (3×20 mL). Organic solvent was eliminated and the residue was submitted to flash chromatography (hexane/ethyl acetate mixtures) to yield the corresponding diester (±)-5.

The synthetic route of 61644-18-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Torres, Susana Y.; Ochoa, Estael; Verdecia, Yamila; Rebolledo, Francisca; Tetrahedron; vol. 70; 31; (2014); p. 4675 – 4684;,
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Adding a certain compound to certain chemical reactions, such as: 6627-89-0, name is tert-Butyl phenyl carbonate, 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 6627-89-0, Formula: C11H14O3

Intermediate 130; 1,1-dimethylethyl (2-amino-2-methylpropyl)carbamate; To a solution of 2-methyl-1 ,2-propanediamine (300 mg, 3.40 mmol) in ethanol (15 ml) was added phenyl-tBu-carbamate (1.32 g, 6.80 mmol). The reaction mixture was stirred at 800C overnight. The solvent was evaporated, water was added and HCI 1 N until pH=3. The mixture was washed with dichloromethane (2 times). The aqueous phase was basified with NaOH 1 N until pH=11-12 and was extracted with dichloromethane (4 times). The organic phase was dried over Na2SO4, filtered and concentrated to give the title compound as colourless liquid (422 mg, 66%). LC/MS : m/z 189 (M+23)+, Rt: 1.62 min.

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; SMITHKLINE BEECHAM CORPORATION; WO2009/47240; (2009); A1;,
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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 121-98-2 as follows. Recommanded Product: Methyl 4-methoxybenzoate

To a cooled (-20 C) solution of 4-methoxybenzoic acid methyl ester 11 (3.00 g, 18.1 mmol) in MeCN (30 mL) was added HBF4·Et2O (3.22 mL, 19.9 mmol) and then slowly added NBS (3.54 g, 19.9 mmol) under less than -10 C. After the addition, the cooling bath was removed and the reaction mixture was allowed to warm up to room temperature, and stirred for 23 h. Saturated NaHSO3 solution was then added, and the reaction mixture was extracted with EtOAc. The combined organic layers were washed with saturated NH4Cl solution and brine, dried over Na2SO4, and then concentrated in vacuo. Purification by silica gel column chromatography (hexane/EtOAc = 5/1) gave 12 (4.35 g, 17.7 mmol, 98%) as a colorless powder;

According to the analysis of related databases, 121-98-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ogura, Tetsuhiro; Usuki, Toyonobu; Tetrahedron; vol. 69; 13; (2013); p. 2807 – 2815;,
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Synthetic Route of 4891-38-7, 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. 4891-38-7, name is Methyl Phenylpropiolate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A representative procedure of skeleton 1 is as follows: CuI (190 mg, 1.0 mmol), Et3N (200 mg, 2.0 mmol) and different alkynes 6a-h (1.0 mmol) were added to a solution of compound 5a (110 mg, 0.4 mmol) in anhydrous DMF (4 mL) at rt. The reaction mixture was stirred at 80 C for 2 h, then cooled to rt. Saturated NaHCO3(aq) (5 mL) was added to the reaction mixture and the solvent was evaporated under reduced pressure. The residue was extracted with EtOAc (3 x 30 mL). The combined organic layers were washed with brine,dried, filtered and evaporated under reduced pressure to afford crude product. Purification on silica gel (hexanes/EtOAc = 2/1-1/2) afforded compounds 1a-h.

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

Reference:
Article; Chang, Meng-Yang; Tai, Hang-Yi; Synthetic Communications; vol. 43; 24; (2013); p. 3363 – 3372;,
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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. 25662-28-6, name is Methyl 1-cyclopentene-1-carboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C7H10O2

EXAMPLE 20 2-(Piperidin-4-ylsulfanyl)cyclopentanecarboxylic acid methyl ester methyl 1-cyclopentene-1-carboxylate (0.24 ml) and Intermediate 12 (0.50 g) were dissolved in anhydrous methanol (20 ml), degassed with nitrogen, and cooled to -10 to -15 C. sodium bis(trimethylsilyl)amide, 1.0 M in tetrahydrofuran (1.93 ml) was added and the reaction stirred for 18 h, warming to room temperature.The reaction mixture was then evaporated and the residue partitioned between ethyl acetate (20 ml) and water (20 ml).The aqueous was extracted once more with ethyl acetate (10 ml) and the combined organic extracts were washed with 2% aqueous citric acid (20 ml), water (20 ml), saturated sodium bicarbonate (20 ml), saturated brine (20 ml), dried (Na2SO4) and evaporated under reduced pressure. The resultant amber oil was dissolved in dichloromethane (10 ml) and treated with trifluoroacetic acid (2 ml).After stirring at room temperature for 17 h, the solvents were evaporated and the residue azeotroped with 1:1 dichloromethane/hexane (3*20 ml).The residue was then dissolved in water (30 ml) and washed with diethyl ether (2*10 ml) before being basified with sodium carbonate to PH 11 and extracted with ethyl acetate (4*15 ml).The combined ethyl acetate extracts were then washed with saturated brine (10 ml), dried (Na2SO4) and reduced in vacuo to provide the title compound as a colourless gum (0.15 g, 31%). TLC Rf 0.26 (6% methanol/dichloromethane containing a trace of aqueous ammonia) MS 244 (MH+)

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; Montana, John Gary; Baxter, Andrew Douglas; Owen, David Alan; Watson, Robert John; US2003/236416; (2003); A1;,
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Electric Literature of 344-14-9,Some common heterocyclic compound, 344-14-9, name is Dimethyl 2-fluoromalonate, molecular formula is C5H7FO4, 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: [Pd(C3H5)Cl]2 (0.004 mmol, 4 mol%), [6-(allyloxymethyl)-N-(2-((R)-((S)-1-(3,5-dimethoxyphenyl)propyl)sulfinyl)phenyl)picoli-namide] (6b, 0.008 mmol, 8 mol%), and (E)-1,3-disubstituted allyl acetates 7 (0.1 mmol) were dissolved in THF (2.0 mL) in a dry Schlenk tube filled with argon. The reaction mixture was stirred for 30 min at room temperature. Then Cs2CO3 (3.0 equiv) and dimethyl 2-fluoromalonate 8 (0.3 mmol, 3.0 equiv) were added. After the completion of the reaction monitoring by TLC, the crude reaction mixture was filtrated with celite and the solvent was removed under reduced pressure. The crude residue was purified by flash column chromatography (petroleum ether/ethyl acetate) to give the desired products 9.

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

Reference:
Article; Zhang, Min; Zhao, Mingzhu; Zheng, Purui; Zhang, Hongbo; Zhao, Xiaoming; Journal of Fluorine Chemistry; vol. 189; (2016); p. 13 – 21;,
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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. 35179-98-7, name is Chloromethyl ethyl carbonate, A new synthetic method of this compound is introduced below., SDS of cas: 35179-98-7

Sodium IODIDE (25 MG) was dissolved in acetonitrile (0. 15 mL) in which had been dissolved chloromethyl ethyl carbonate (22 mg) [Z. Li et al. , Bioorg. Med. CHEM. LETT., 7,2909 (1997)], and the solution was stirred for four hours under dark room conditions at room temperature. Next, the solution was added to DMF (0. 30 mL) in which had been dissolved BOC–ALA-HIS (TRT) (30 mg) and DIISOPROPYLETHYLAMINE (0. 019 ML), and stirring was further carried out for 3 days at room temperature. After that, ethyl acetate (30 mL) was added to the solution obtained, and the solution was washed with a sodium hydrogencarbonate aqueous solution (5 mL) twice and a sodium chloride aqueous solution (5 ML) once. After the washing, drying was carried out with sodium sulfate, concentration was carried out under reduced pressure, the concentrate was dissolved in a mixed liquid of acetonitrile and water (1: 4), and then freeze drying was carried out, thus obtaining A white powder (approximately 55 mg). The powder was treated for 30 minutes with TFA (1.2 ML) CONTAINING 2% TRIISOPROYLSILANE and 2% water, and then washing was carried out three times with ether (10 mL). The residue was dissolved in a mixed solution of acetonitrile and water (1: 4), and then freeze drying was carried out, thus obtaining 28 mg of crude product. The crude product obtained was subjected to HPLC (with an ODS column) with the undermentioned conditions using water- acetonitrile containing 0. 1T TFA as an eluent, the fraction containing THE TARQET COMPOUND (ss-ALA-HIS-OCH2-OCO-OCH2CH3) was isolated using the absorbance at 220 nm as an indicator, and freeze drying was carried out, thus obtaining a white powder (19 mg) of P-ALA-HIS-OCH2-OCO-OCH2CH3 (TFA salt). This powder was dissolved in a 0. 05 M HC1 aqueous solution containing 5% acetonitrile, and freeze drying was again carried out, whereby the target compound (-ALA-HIS-OCH2-OCO-OCH2CH3 2HC1) WAS obtained as a white powder (11 mg, 52T yield). LT;HPLC CONDITIONS GT; Column : Cosmosil 5C18-MS 10 x 250 mm Eluent : Solution A: Water containing 0. 1% TFA Solution B: Acetonitrile containing 0. 1% TFA Concentration gradient Time (min) 0 20 25 Solution B % 5 15 95 Flow rate : 2.5 ML/MIN -H NMR (400 MHz, DMSO-d6, 25C) : No. 1. 23 (3H, t, J = 7.1 Hz), 2.46-2. 58 (2H, m), 2. 88-2. 98 (2H, m), 3.07 (1H, dd, J = 8.8 and 15.1 Hz), 3.16 (1H, dd, J = 5.7 and 15. 1 Hz), 4.19 (2H, q, J = 7.1 Hz), 4.58-4. 66 (1H, m), 5.69 (1H, d, J = 6.1 Hz), 5.72 (1H, d, J = 6. 1 HZ), 7.44 (1H, s), 7. 87 (3H, br), 8.87 (1H, d, J = 7.2 Hz), 9. 01 (1H, S), 14.35 (2H, br) ; DUC NOR (100 MHz, DMSO-DS, 25C) : 8 13.9, 25. 6,31. 8,34. 9, 51.3, 64.5, 82.4, 117. 2, 128.6, 133.9, 153.1, 169. 3, 169. 8; ESI-MS: m/z 329 (M+H) ; calculated for CL3H2LN406 : 329.

The synthetic route of 35179-98-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OSAKA INDUSTRIAL PROMOTION ORGANIZATION; OSAKA UNIVERSITY; WO2005/9471; (2005); 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. 20372-66-1, name is Methyl 2,4,5-trifluorobenzoate, A new synthetic method of this compound is introduced below., Formula: C8H5F3O2

Methyl 2,4,5-trifluorobenzoate (DSL Chemicals, 950 mg, 5 mmol), sodium cyanide (306 mg, 6.25 mmol) and tetrabutylammonium bromide (2.01 g, 6.25 mmol) were dissolved in DMF (10 mL) and the resulting mixture was heated at 600C overnight. Additional amount of sodium cyanide (306 mg, 6.25 mmol) was added and the mixture was stirred at 600C for 24 additional hours. The reaction mixture was diluted with EtOAc and washed with brine several times. The organic layer was dried over MgSO4 and concentrated under vacuum. The residue was purified by flash chromatography (silica, EtOAc/cHex) to give the title compound. 1H NMR (DMSO-dbeta, 300 MHz) delta 7.77 (dd, J=8.4, 5.5 Hz, 1 H), 7.42 (dd, J=8.9, 5.0 Hz, 1 H), 3.96 (s, 3H). LC/MS (Method B): 463.2 (M-H)”, 465.2 (M+H)+. HPLC (Method A) Rt 3.63 min (Purity: 99.9%).

The synthetic route of 20372-66-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SERONO S.A.; QUATTROPANI, Anna; MONTAGNE, Cyril; SAUER, Wolfgang; CROSIGNANI, Stefano; BOMBRUN, Agnes; WO2010/112461; (2010); A1;,
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Synthetic Route of 94994-25-9, These common heterocyclic compound, 94994-25-9, name is Methyl 4-formylbicyclo[2.2.2]octane-1-carboxylate, 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.

EXAMPLE 21 4-[4-Benzo[1,3]dioxol-5-yl-5-(6-methyl-pyridin-2-yl)-1H-imidazol-2-yl]-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester 4-Formyl-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester (0.284 g, 1.0 mmol) was added to a solution of 1-benzo[1,3]dioxol-5-yl-2-(6-methyl-pyridin-2-yl)-ethane-1,2-dione 2-oxime (see Example 4; 0.215 g, 1.1 mmol) and ammonium acetate (1.54 g, 20 mmol) in acetic acid (5 mL). The mixture was refluxed for 2 hours. Solvent was removed under reduced pressure. The reaction mixture was then quenched with ammonia/ice mixture. The aqueous solution was extracted with ethyl acetate. Ethyl acetate extract was washed with brine, dried over sodium sulfate, filtered, and concentrated to give 0.300 g (65%) of the hydroxyimidazole as a yellow solid. MS (ESP+) m/z 462.3 (M+1).

Statistics shows that Methyl 4-formylbicyclo[2.2.2]octane-1-carboxylate is playing an increasingly important role. we look forward to future research findings about 94994-25-9.

Reference:
Patent; Lee, Wen-Cherng; Sun, Lihong; Shan, Feng; Chuaqui, Claudio; Zheng, Zhongli; Petter, Russell C; US2006/63809; (2006); 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. 2150-37-0, name is Methyl 3,5-dimethoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C10H12O4

Step 1: Intermediate 1 [00789j To a solution of methyl 3,5-dimethoxybenzoate (2.00 g, 10.2 mmol) in CH3CN (20 mL), 1 -(chloromethyl)-4-fluoro- 1 ,4-diazoniabicyclo [2.2 .2]octane ditetrafluoroborate (SelectfluorTM, 5.40 g, 15.2 mmol) was added. The reaction was stirred at room temperature overnight after which it was diluted with water and extracted with ethyl acetate. The organic layers were washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The resultant residue was purified by column chromatography (hexane/ethyl acetate: 10/1) to afford the title compound as white solid (800 mg, 38 %). ?H NMR (400 MHz, CDC13): oe 3.81 (s, 3H), 3.87 (s, 3H), 3.93 (s, 3H), 6.70 (dd, 1H), 6.91 (dd, 1H).

The synthetic route of 2150-37-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; SANOFI; D’AGOSTINO, Laura Akullian; SJIN, Robert Tjin Tham; NIU, Deqiang; MCDONALD, Joseph John; ZHU, Zhendong; LIU, Haibo; MAZDIYASNI, Hormoz; PETTER, Russell C.; SINGH, Juswinder; BARRAGUE, Matthieu; GROSS, Alexandre; MUNSON, Mark; HARVEY, Darren; SCHOLTE, Andrew; MANIAR, Sachin; WO2014/144737; (2014); A1;,
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