Tag: M.W=100-200

Application of 55414-72-7, 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. 55414-72-7, name is (2-Amino-5-methoxyphenyl)methanol, molecular formula is C8H11NO2, The 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.

Compound 21 (120 mg, 0.72 mmol) and EDC.HCl (165 mg, 0.86 mmol) were dissolved in DMF(2 mL) and stirred for 5 minutes. To this mixture at 0 C was added a solution of 1-hydroxybenzotriazole (116 mg, 0.86 mmol) and compound 4 (132 mg, 0.86 mmol) in DMF (1mL),followed by DIPEA (0.18 mL, 1.08 mmol). The reaction mixture was stirred under N2 atmosphere atroom temperature for 24 h. The solvent was evaporated under reduced pressure. The crude product was dissolved in HCl (5 mL, 1N) and ethyl acetate (10 mL). After partitioning of the two layers, the aqueous layer was extracted with ethyl acetate (4 x 15 mL). All organic layers were combined and washed with water (10 x 20 mL). Finally the organic layer was dried with MgSO4 and evaporated onto silica. The crude product was purified by column chromatography, eluting with 1:4 ethylacetate/dichloromethane, to produce the title compound as a moist white solid (118 mg, 55%) and 23 asa yellow solid (50 mg, 27%). Data for 22: m.p. 144-146 C; IR (neat) vmax (cm-1) 3232, 3071, 2918,2864, 2712, 2450, 2284, 2111, 2069, 1647, 1580, 1521; 1H NMR (400 MHz, CDCl3) delta 8.56 (s, 1H,NH), 8.11 (d, J = 8.1 Hz, ArH3), 7.97 (d, J = 8.7 Hz, ArH6), 7.68 (m, 3H, ArH4, ArH6, ArH5), 6.93(d, J = 8.7 Hz, ArH5), 6.81 (s, 1H, ArH3), 4.74 (s, 2H, CH2), 3.82 (s, 3H, OCH3) 3.96 (s, H, OH);13C{1H} NMR (101 MHz, CDCl3) delta 164.9 (C=O), 157.2 (C4), 146.8 (C2), 134.0 (C4), 133.2 (C1),132.7 (C1), 130.9 (C6), 129.5 (C2), 128.9 (C5), 125.3 (C6), 124.9 (C3), 113.8 (C5), 64.5 (CH2), 55.7(OCH3); HRMS (ESI, +ve) C15H14N2O5Na+ [MNa+] requires m/z 325.0795, found 325.0772. Data for 23: m.p. 135-137 C; IR (neat) vmax (cm-1) 3235, 3069, 2646, 2321, 2103, 1920, 1729, 1655,1523; 1H NMR (400 MHz, CDCl3) delta 8.30 (s, 1H, NH), 8.14 (d, J = 8.2 Hz, ArH), 7.84-7.81 (m, 2H,ArH), 7.75-7.61 (m, 6H, ArH), 7.03-6.98 (m, 2H, ArH), 5.36 (s, 2H, CH2), 3.83 (s, 3H, OCH3);13C{1H} NMR (101 MHz, CDCl3) delta 166.0, 165.7, 157.9, 148.0, 146.5, 134.1, 133.3, 133.0, 132.3, 130.8, 130.3, 129.1, 129.0, 128.8, 127.5, 127.0, 124.8, 124.0, 116.8, 115.9, 65.7, 55.7; HRMS (ESI,+ve) C22H17N3O8Na+ [MNa+] requires m/z 474.0928, found 474.0882.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 55414-72-7, (2-Amino-5-methoxyphenyl)methanol.

Reference:
Article; Lizarme, Yuvixza; Wangsahardja, Jonatan; Marcolin, Gabriella M.; Morris, Jonathan C.; Jones, Nicole M.; Hunter, Luke; Bioorganic and Medicinal Chemistry; vol. 24; 7; (2016); p. 1480 – 1487;,
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Adding a certain compound to certain chemical reactions, such as: 14002-80-3, Methyl 3-hydroxy-2,2-dimethylpropanoate, 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, Quality Control of Methyl 3-hydroxy-2,2-dimethylpropanoate, blongs to alcohols-buliding-blocks compound. Quality Control of Methyl 3-hydroxy-2,2-dimethylpropanoate

EXAMPLE 106a Preparation of intermediate 2,2-dimethyl-3-(toluene-4-sulfonyloxy)-propionic acid methyl ester To a mixture of 3-hydroxy-2,2-dimethyl-propionic acid methyl ester (13.2 g, 0.1 mol), K2CO3 (20 g, 0.14 mol) and DMAP (6.2 g, 0.05 mol) in DCM (100 mL) was added p-toluenesulfonyl chloride (19 g, 0.1 mol). The mixture was stirred at room temperature overnight, then filtered. The filtrate was washed with HCl aq. (1 M) and water, dried over anhydrous Na2SO4 and concentrated to give the title compound (15 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14002-80-3, Methyl 3-hydroxy-2,2-dimethylpropanoate, and friends who are interested can also refer to it.

Reference:
Patent; Ding, Qingjie; Jiang, Nan; Yang, Song; Zhang, Jing; Zhang, Zhuming; US2009/156610; (2009); A1;,
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Electric Literature of 23147-58-2 , The common heterocyclic compound, 23147-58-2, name is Glycerol aldehyde dimer, molecular formula is C4H8O4, 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.

Step 1: 2-(2-hydroxyethyl)-5-methoxy-1-indanone A solution of 5-methoxy-1-indanone (500 mg, 3.08 mmol) in methanol (10 mL) was treated with 10% palladium on carbon (53 mg) followed by glycoaldehyde dimer (370 mg, 3.08 mmol) and 0.5M sodium methoxide in methanol (1.3 mL, 0.65 mmol). The mixture was placed under a hydrogen atmosphere (balloon) and stirred vigorously at room temperature for 65 hours. After purging with nitrogen, the mixture was filtered through a 0.45 mum Acrodisc and the disk was rinsed with methanol (2 mL). The filtrate was diluted with EtOAc (25 mL), washed with 0.1N HCl (15 mL) and brine (15 mL), dried over MgSO4, filtered, and evaporated under vacuum to a solid. LC-MS of this material showed a mixture of starting material (major) and product. The mixture was purified by chromatography on a Biotage Flash 12M KP-Sil column (12 mm*15 cm). The column was eluted with 3:2 EtOAc-hexanes, collecting 6 mL fractions every 30 sec. Fractions 20-36 were concentrated under vacuum and flashed with benzene to afford 2-(2-hydroxyethyl)-5-methoxy-1-indanone as an oil. 1H NMR (CDCl3, 500 MHz) delta 1.80 and 2.05 (two m, CH2CH2OH), 2.79 and 3.35 (two dd, 3-CH2), 2.83 (m, H-2), 3.77-3.90 (m, CH2CH2OH), 3.87 (s, OCH3), 6.86 (d, H-4), 6.89 (dd, H-6), and 7.67 (d, H-7).

The synthetic route of 23147-58-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wilkening, Robert R.; Fried, Amy; US2006/94779; (2006); A1;,
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Reference of 3840-31-1, 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. 3840-31-1, name is (3,4,5-Trimethoxyphenyl)methanol. A new synthetic method of this compound is introduced below.

General procedure: The compound (3,4,5-trimethoxyphenyl)-methanol 15 (4.5 mmol) was dissolved in THF (15 mL) and added to a stirred suspension of NaH (60%, 5.4 mmol) in THF (5 mL) at 0 C. The reaction mixture was stirred for 30 min at the same temperature. Propargyl bromide (4.9 mmol) was added to the reaction mixture at the same temperature and stirring was continued for an additional 5 h at room temperature. After completion the reaction (TLC), the reaction mixture was quenched with ice water and extract with ethyl acetate (2 * 20 mL). The organic extract was washed with brine, dried over Na2SO4, and solvent removed under reduced pressure. The residue was subjected to silica gel column chromatography purification (ethyl acetate/hexane 1:10) to afford 1,2,3-trimethoxy-5-((prop-2-yn-1-yloxy)methyl)benzene 16.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3840-31-1, (3,4,5-Trimethoxyphenyl)methanol, and friends who are interested can also refer to it.

Reference:
Article; Suman; Murthy, T. Ramalinga; Rajkumar; Srikanth; Dayakar; Kishor, Chandan; Addlagatta, Anthony; Kalivendi, Shasi V.; Raju, B. China; European Journal of Medicinal Chemistry; vol. 90; (2015); p. 603 – 619;,
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Synthetic Route of 50595-15-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 50595-15-8, name is tert-Butyl 2-hydroxyacetate. This compound has unique chemical properties. The synthetic route is as follows.

A stirred suspension of 88 mg (2.2 mmol) sodium hydride (60percent dispersion in mineral oil) in 5 ml of dry dimethylformamide at -5¡ã C. under nitrogen was treated with 264 mg (2 mmol) tert-butylglycolate. After 10 minutes 298 mg (2 mmol) of 3,6-dichloropyridazine (Aldrich D7, 320-0) was added and the solution was allowed to warm to room temperature and was stirred overnight. The volatiles were evaporated under reduced pressure and the residue was chromatographed on silica eluding with ethyl acetate/hexane (1:2) to give 210 mg of a gum that was dissolved in 20 ml of ethanol and treated with 10percent palladium on carbon (Fluka) and hydrogenated under a hydrogen atmosphere overnight. The catalyst was removed by filtration and the volatiles were evaporated under reduced pressure to give a gum that was chromatographed on silica eluding with ethyl acetate/hexane (1:2) followed by ethyl acetate to give 50 mg of a gum [M+H+MeCN]+252. The gum was dissolved in 2 ml of dichloromethane and treated with 1 ml of trifluoroacetic acid. After 10 minutes the volatiles were evaporated and the residue triturated with toluene and re-evaportated to give a gum that was further triturated with petroleum ether bp 40-60¡ã C. to give 2-(3-pyrazinyloxy)acetic acid trifluoroacetate.

According to the analysis of related databases, 50595-15-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US6472404; (2002); B1;,
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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. 13807-89-1, name is 2-((4-Methoxybenzyl)oxy)ethanol. This compound has unique chemical properties. The synthetic route is as follows. Safety of 2-((4-Methoxybenzyl)oxy)ethanol

(1) Synthesis of ethylene glycol protected by azidochlorobenzyl group and methoxybenzyl group: synthesis of 1-azido-2-chloro-4-(4-methoxybenzyloxyethoxymethyl)benzene. 2-(4-Methoxybenzyloxy)ethanol (500 mg, 2.75 mmol) was dissolved in DMF (10 ml), and sodium hydride (60% in oil, 132 mg, 3.30 mmol) was added at 0 C., which was followed by stirring for 30 min. Then 4-azido-3-chlorobenzyl bromide (813 mg, 3.30 mmol) was added portionwise. The resulting mixture was stirred at 0 C. for 30 min and at room temperature for 2 hr. Ice-water was added and the mixture was extracted with ether. The ether layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=10:1) to give the title compound as a yellow oil (805 mg, yield 84%). 1 H-NMR (270 MHz, CDCl3) delta: 7.39(d,1H), 7.30-7.24(m,3H), 7.13(d,1H), 6.90-6.85(m,2H), 4.51(s,4H), 3.80(s,3H), 3.64(s,4H)

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, 13807-89-1, 2-((4-Methoxybenzyl)oxy)ethanol.

Reference:
Patent; Wako Pure Chemical Industries, Ltd.; US5998595; (1999); A;,
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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. 945-24-4, name is (2,4-Diaminopteridin-6-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. Formula: C7H8N6O

2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride (4.40 g, 19.2 mmol) was dissolved in hot water (150 mL) and after cooling to 21 C the solution was neutralized with 1M NaOH aq. solution to pH 7 (ca. 20 mL) . The formed precipitates were collected by filtration, washed with water, and dried in vacuo over P205 to afford an orange-beige solid corresponding to 2,4-diamino-6- (hydroxymethyl)pteridine. The solid was suspended in dry DMAc (25 mL) and triphenylphosphine dibromide ( 18.1 g, 42.9 mmol) was added to the suspension. The turbid and dark mixture was stirred for 24 h at 20 C under a N2 atmosphere. Then 4-aminobenzoic acid (2.97 g, 19.6 mmol) was added to the reaction and stirred for 3 additional days. The reaction mixture was poured into 250 mL of 0.33M NaOH and the precipitate was filtered off. The filtrate was neutralized with 10% aq . acetic acid (ca. 20 mL and the precipitate form upon neutralization was filtered, washed with water, triturated with MeOH, filtered, and dried in vacuo to afford 7 as an orange-beige solid (5.70 g, 91%) . XH NMR (400 MHz, DMSO-d5) delta 12.15 (br s, 1H), 8.63 (s, 1H), 8.17 (br s, 1H), 7.94 (br s, 1H), 7.73 (d, J = 9.0 Hz, 2H), 7.04 (br s, 2H), 6.83 (d, J = 9.0 Hz, 2H), 4.81 (s, 2H), 3.23 (s, 3H); 13C NMR (101 MHz, DMSO-d5) delta 167.8, 163.2, 161.1, 152.3, 149.5, 147.8, 131.5, 122.2, 118.1, 111.7, 100.0, 55.2, 39.6.

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, 945-24-4, (2,4-Diaminopteridin-6-yl)methanol.

Reference:
Patent; DANMARKS TEKNISKE UNIVERSITET; PEIRO CADAHIA, Jorge; CLAUSEN, Mads, Hartvig; BONDEBJERG, Jon; HANSEN, Christian, Abildgaard; (101 pag.)WO2018/37120; (2018); A1;,
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Synthetic Route of 15852-73-0, Adding some certain compound to certain chemical reactions, such as: 15852-73-0, name is (3-Bromophenyl)methanol,molecular formula is C7H7BrO, 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 15852-73-0.

General procedure: A mixture of alcohol (0.75 mmol), and catalyst Mo1 (13 mg,3.0 mol%) taken in 0.5 mL of water was stirred at 100 C under oxygenatmosphere (O2 bladder) and the stirring was continued for16-24 h as per requirement. The progress of reaction was monitoredby TLC. After completion of the reaction, ethyl acetate was added to the mixture. The aqueous phase was extracted with ethyl acetate 2-3 times. Then the combined organic extracts were driedover anhydrous sodium sulfate and the solvent was removed under reduced pressure. The crude product so obtained was purified by column chromatography using hexane-ethyl acetate as eluent. While the known products were characterized by spectroscopic techniques and compared with reported data and the new products 22b and 36b were characterized completely. The characterization detail is provided in supporting information section.

According to the analysis of related databases, 15852-73-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Thiruvengetam, Prabaharan; Chakravarthy, Rajan Deepan; Chand, Dillip Kumar; Journal of Catalysis; vol. 376; (2019); p. 123 – 133;,
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Adding a certain compound to certain chemical reactions, such as: 10488-69-4, Ethyl 4-chloro-3-hydroxybutanoate, 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, Recommanded Product: 10488-69-4, blongs to alcohols-buliding-blocks compound. Recommanded Product: 10488-69-4

Example 21 : pH profiles of enzymatic and nonenzymatic test reactions of ethyl 4-chloro- 3-hydroxybutyrate with cyanide Aqueous solutions containing 25 MG/ML sodium cyanide were prepared at pH 5.0, 6.0, 7.0, 7.5, 8. 0, 8. 5, and 9.0 by the addition of 85percent phosphoric acid while monitoring with pH meter. 5 mL of each solution was charged to a SEPARATE 20 ML screw cap vial. Halohydrin dehalogenase SEQ ID NO: 38 (20 mg) was added to each vial, followed by ethyl (S)-4-chloro-3-hydroxybutyrate (50 mg, 0.30 mmoles). For nonenzymatic reactions experiments, the procedure was identical with the exception that the enzyme was omitted. The vials were capped and heated in an oil bath at 55 ¡ãC for 3 hrs, then removed and cooled to room temperature. A 0.4 mL sample of each reaction mixture was extracted with 1 mL butyl acetate and the extracts were analyzed by gas chromatography. The analyzed amounts of substrate and products in each vial are given in Table I, and graphed vs. pH in Figure 1. IN BOTH, CHLOROHYDRIN means ethyl (S)-4-chloro-3- hydroxybutyrate, cyanohydrin means ethyl (R)-4-CYANO-3-HYDROXYBUTYRATE, and crotonate means ethyl 4-hydroxycrotonate. In the Table, ND means not detected. Table I : Millimoles CHLOROHYDRIN, cyanohydrin and crotonate by-product analyzed in test reactions with and without HALOHYDHN dehalogenase. See Example 21 without halohydrin dehalogenase with halohydrin dehalogenase mmol mmol mmol mmol mmol mmol PH chlorohydrin cyanohydrin crotonate chlorohydrin cyanohydrin crotonate 5.0 0. 33 ND ND 0. 27 ND ND 6. 0 0. 29 ND ND 0. 07 0. 20 ND 7. 0 0. 30 ND ND 0. 01 0. 28 ND 7.5 0.3 ND ND 0. 004 0. 30 ND 8. 0 0.30 0.01 ND 0.002 0.29 ND 8. 5 0. 21 0. 05 0. 001 0. 001 0. 24 ND 9. 0 0.11 0.10 0.002 0.001 0.21 ND The pHs of the final test reaction mixtures were remeasured. For the mixtures including halohydrin dehalogenase with initial pHs of 7 or above (being the mixtures in which near complete conversion of the CHLOROHYDRIN to the cyanohydrin occurred, the final mixture pHs were 0.4 to 0.6 pH units below the initial pHs. The other mixtures showed much lesser changes in pH from their initial values. These data show that under these reaction conditions and time, no measurable nonenzymatic reaction of the ethyl 4-CHLORO-3-HYDROXYBUTYRATE with cyanide occurred at any tested pH less than 8. At pH 8 and above, increasing nonenzymatic reaction with cyanide to form ethyl 4-cyano-3-hydroxybutyrate occurred with increasing pH and was accompanied by increasing formation of ethyl 4-hydroxycrotonate by-product. In contrast, the enzymatic reaction with halohydrin dehalogenase occurred at all the tested pH’s greater than 5 and with no detectable formation of ethyl 4-hydroxycrotonate at any tested pH. Additionally, for both enzymatic and nonenzymatic test reactions at pH greater than 8, the mole total of the GC- analyzed products decreased from the initial 0.30 MMOLES provided (as ethyl 4-chloro-3- hydroxybutyrate reactant) indicating the increasing formation of non-analyzable by-products with increasing pH greater than 8. It was separately established that the ester group of the reactant and product are increasingly HYDROLYZED to carboxylic acid groups at pHs greater than 8 and that the resulting carboxylic acids are not extracted in to the extracts of reaction mixture samples that are analyzed by GC. See Example 22.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10488-69-4, Ethyl 4-chloro-3-hydroxybutanoate, and friends who are interested can also refer to it.

Reference:
Patent; CODEXIS, INC.; WO2005/18579; (2005); A2;,
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Application of 3597-91-9, 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 3597-91-9 as follows.

Step 1. Preparation of biphenyl-4-ylmethy. 2,2,2-trichloroethanimidoate (C93). A suspension of biphenyl-4-yimethanol (36.8 g, 200 mmol) in dichloromethane (240 mL) was treated with 50% aqueous potassium hydroxide solution (160 mL). The reaction mixture was cooled to 0″C, and maintained at 0 – 1OC as tetra-rt-butylammonium sulfate (1.18 g, 2,0 mmol) was added, followed by a slow addition of trichtoroacetonitrile (25.1 mL, 250 mmol) over 10 minutes. The reaction was stirred at OC for an hour, and then stirred at 25C for an additional hour, after which the organic layer was filtered through a short pad of Celite on top of a layer of silica gel. The pad was rinsed with additional methylene chloride (1500 mL), and the elubetants were concentrated in vacuo to provide C93 as a white solid, which was used in the next step without purification. Yield: 66.1 g, quantitative. LCMS m/z 167.2 (C13H1 1′). 1H NMR (400 MHz, CDCI3) 6 5.40 (s, 2H), 7,37 (m, 1 H), 7.46 (m, 2H), 7.52 (d, J?8.7 Hz, 2H), 7,62 (m, 4H), 8.43 (br s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3597-91-9, its application will become more common.

Reference:
Patent; PFIZER INC.; BROWN, Matthew Frank; DONOVAN, Charles Francis; ELLSWORTH, Edmund Lee; HOYER, Denton Wade; JOHNSON, Timothy Allen; LALL, Manjinder Singh; LIMBERAKIS, Chris; MURPHY, Sean Timothy; SHERRY, Debra Ann; TAYLOR, Clarke Bentley; WARMUS, Joseph Scott; WO2010/32147; (2010); A2;,
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