Month: September 2021

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, category: alcohols-buliding-blocks, blongs to alcohols-buliding-blocks compound. category: alcohols-buliding-blocks

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 °C 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.

The synthetic route of 10488-69-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CODEXIS, INC.; WO2005/18579; (2005); A2;,
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Electric Literature of 5339-85-5 , The common heterocyclic compound, 5339-85-5, name is 2-(2-Aminophenyl)ethanol, molecular formula is C8H11NO, 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.

2-(Aminophenyl)ethanol(11, 2.4 g, 20 mmol, 1.0 equiv) was dissolved in CH2Cl2(40 mL, abs.) and cooled to 0 C. Pyridiniumchlorochromate(PCC, 13, 6.5 g, 30 mmol, 1.5 equiv) was added in small portions.The mixture was kept at 0 C for 1 h and then stirred for 4 h at room temperature. Silica was added to the mixture and the solvent was evaporated. Purification was performed by distillation. Yield 71.9%. 1H NMR (500 MHz, DMSO) d 6.60(s, 2H), 6.66 (d, J = 8.1 Hz, 1H), 6.73-6.77 (m, 1H), 7.27-7.32(m, 1H), 7.45 (d, J = 8.2, 1H), 9.89 (s, 1H). 13C NMR (126 MHz,DMSO) d 115.5, 116.2, 118.4, 134.9, 135.5, 149.3, 193.1.C7H7NO. MS (ESI+): m/z 122.6 (4.5, (M+H)+), 144.6 (100,(M+Na)+). (agrees with28)

The synthetic route of 5339-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Merk, Daniel; Gabler, Matthias; Gomez, Roberto Carrasco; Flesch, Daniel; Hanke, Thomas; Kaiser, Astrid; Lamers, Christina; Werz, Oliver; Schneider, Gisbert; Schubert-Zsilavecz, Manfred; Bioorganic and Medicinal Chemistry; vol. 22; 8; (2014); p. 2447 – 2460;,
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Reference of 4541-14-4, 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. 4541-14-4, name is 4-(Benzyloxy)butan-1-ol. A new synthetic method of this compound is introduced below.

4-Benzyloxy-butan-1-ol (5.0 g), potassium bromide (0.66 g), and 2,2,6,6-tetramethylpiperidine 1-oxyl free radical (43.1 mg) were mixed in toluene (15 mL), ethyl acetate (15 mL), and water (3 mL). To the reaction solution were added dropwise a mixed solution of potassium hydrogen carbonate (5.55 g) in water (15 mL) and then 15 w/w/o aqueous sodium hypochlorite solution (16.5 mL) under ice cooling. The reaction solution was stirred under ice cooling for 1.5 hours. To the reaction solution was added 15 w/w % aqueous sodium hypochlorite solution (4 mL), and the reaction solution was stirred for additional 2 hours. The reaction solution was extracted with toluene. The organic layer was washed sequentially with water, a mixed solution of potassium iodide (73 mg) in 1M hydrochloric acid (5 mL), a mixed solution of sodium thiosulfate (2.3 g) and potassium carbonate (4.02 g) in water (8.3 mL), and aqueous saturated sodium chloride solution, and dried over magnesium sulfate. After removing magnesium sulfate on a filter, the filtrate was concentrated under reduced pressure to give the titled compound (4.08 g) as a crude product. (0850) 1H-NMR (400 MHz, CDCl3) 1.91-1.99 (m, 2H), 2.55 (td, J=7.05, 1.62 Hz, 2H), 3.51 (t, J=6.13 Hz, 2H), 4.49 (s, 2H), 7.15-7.37 (m, 5H), 9.79 (t, J=1.62 Hz, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4541-14-4, its application will become more common.

Reference:
Patent; JAPAN TOBACCO INC.; YOKOTA, Masahiro; IKENOGAMI, Taku; WATANABE, Eiichi; SEKI, Noriyoshi; SAKAI, Takayuki; FUJIOKA, Shingo; SHIOZAKI, Makoto; SUWA, Katsunori; OGOSHI, Yosuke; NOGUCHI, Masato; MAEDA, Katsuya; (228 pag.)US2016/194290; (2016); A1;,
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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. 23147-58-2, name is Glycerol aldehyde dimer, molecular formula is C4H8O4, 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. Safety of Glycerol aldehyde dimer

Step 1 : Preparation OF 2- (2-HYDROXY-ETHYLAM. no)-benzoic acid methyl ester :; A solution of methyl anthranilate (2. 6 mL, 20 mmol, 1 equiv.) in DCM (60 mL) is treated with glycolaldehyde dimer (1. 20 g, 10 mmol, 0. 5 equiv.) then acetic acid (1. 72 mL, 30 mmol, 1. 5 equiv.) Within 1H a yellow solution had formed, to which was added portionwise sodium triacetoxyborohydride (6. 78 g, 32 mmol, 1. 6 equiv.). After 3 days the reaction is quenched with methanol (25 mL) and the solvent removed IN VACUO. The residue is partitioned between ethyl acetate and 10% aqueous citric acid. The separated aqueous layer is extracted with ethyl acetate three times and the combined organics washed with brine, dried over NA2S04, filtered and concentrated. The crude product is purified by silica gel chromatography (30% ETOAC/HEXANE gradient) to provide the desired product as a white waxy solid (1. 82 g, 47 % YIELD). 1H NMR (400 MHz, CDC13) ; 8 7. 84 (1H, dd, J = 8. 0, 1. 6 Hz) ; 7. 29 (1H, m) ; 6. 68 (1H, d, J = 8. 4 Hz) ; 6. 55 (1H, m) ; 3. 81 (2H, t, J = 5. 5 Hz) ; 3. 78 (3H, s) ; 3. 34 (2H, t, J = 5. 5 Hz).

With the rapid development of chemical substances, we look forward to future research findings about 23147-58-2.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2005/28474; (2005); A2;,
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Application of 1805-32-9, 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. 1805-32-9, name is 3,4-Dichlorobenzyl alcohol. A new synthetic method of this compound is introduced below.

General procedure: To a solution of 18 (100 mg,0.420 mmol) and [4-(trifluoromethyl)phenyl]methanol (111 mg,0.630 mmol) in THF (10.0 mL), PPh3 (178 mg, 0.68 mmol), a 40%diethyl azodicarbonate toluene solution (309 lL, 0.680 mmol)were added at room temperature, and stirred under N2 atmosphereat 60 C for 4 h. After cooling to room temperature, the solvent wasdistilled off under reduced pressure. The residue was purified bysilica gel column chromatography (hexane/AcOEt = 100:0 to 95:5(v/v)) to obtain 19k as colorless oil (125 mg, 75%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1805-32-9, 3,4-Dichlorobenzyl alcohol, and friends who are interested can also refer to it.

Reference:
Article; Takano, Rieko; Yoshida, Masao; Inoue, Masahiro; Honda, Takeshi; Nakashima, Ryutaro; Matsumoto, Koji; Yano, Tatsuya; Ogata, Tsuneaki; Watanabe, Nobuaki; Hirouchi, Masakazu; Kimura, Takako; Toda, Narihiro; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5546 – 5565;,
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Reference of 6338-55-2, 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. 6338-55-2, name is 2-(2-(2-Aminoethoxy)ethoxy)ethanol, molecular formula is C6H15NO3, 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 16 (2.6 g, 17.4 mmol) was dissolved in a mixture of 10 mL of methanol and 5 mL of water,0.695g sodium hydroxide was dissolved in 10mL of water was added to the above solution,Then a solution of (Boc) 2O (4.167 g, 19.1 mmol) in methanol (5 mL) was added and stirred overnight.After the reaction was completed, the solvent was removed by spin-drying, 15 mL of water was added and extracted with dichloromethane (3 * 20 mL). After drying over anhydrous sodium sulfate, the organic solvent was removed and the residue was eluted with 1: 1 EtOAc / Column chromatography gave 2.15 g of compound 17 in 50% yield.

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 6338-55-2, 2-(2-(2-Aminoethoxy)ethoxy)ethanol.

Reference:
Patent; Shanghai Jiao Tong University; Shen Yumei; Yang Qinglai; Tan Lianjiang; Li Xinhui; Shao Zhifeng; Gong Bing; Li Xiaowei; Liu Yazhi; Zhang Zhen; (35 pag.)CN104725453; (2017); B;,
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Adding a certain compound to certain chemical reactions, such as: 83647-43-2, (3-Bromo-2-methylphenyl)methanol, 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, Application In Synthesis of (3-Bromo-2-methylphenyl)methanol, blongs to alcohols-buliding-blocks compound. Application In Synthesis of (3-Bromo-2-methylphenyl)methanol

Perbromomethane (14.35 g, 43.3 mmol) was added portionwise to a solution of (3-bromo-2-methylphenyl)methanol (7.25 g, 36.1 mmol) and triphenylphosphine (11.35 g, 43.27 mmol) in DCM (120 mL) (reaction exotherms to ?40 C.) and the reaction was stirred at room temperature for 2 hours. The residue was passed through a pad of silica, eluting with DCM. The filtrate was concentrated to dryness, then the crude product was purified by flash silica chromatography, elution gradient 0 to 25% EtOAc in heptane. Product fractions were concentrated to dryness to afford 1-bromo-3-(bromomethyl)-2-methylbenzene (8.52 g, 90%) as a colourless oil. 1H NMR (500 MHz, CDCl3, 27 C.) 2.48 (3H, s), 4.52 (2H, s), 6.99-7.05 (1H, m), 7.22-7.27 (1H, m), 7.52 (1H, dd).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,83647-43-2, (3-Bromo-2-methylphenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; AstraZeneca AB; YANG, Bin; VARNES, Jeffrey Gilbert; SCOTT, James Stewart; MOSS, Thomas Andrew; O’DONOVAN, Daniel Hillebrand; NISSINK, Johannes Wilhelmus Maria; HUGHES, Samantha Jayne; BARLAAM, Bernard Christophe; (83 pag.)US2017/305909; (2017); A1;,
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Related Products of 80866-82-6 ,Some common heterocyclic compound, 80866-82-6, molecular formula is C8H9BrO2, 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.

(5-Bromo-2-methoxyphenyl)methanol (1.89 g, 8.71 mmol) was dissolved in 25 mL of dichloromethane. Imidazole (0.711 g, 10.45 mmol) was added, followed by addition of tert-butyldimethylsilyl chloride (1.378 g, 9.14 mmol). After stirring at room temperature for 15 minutes, the reaction was complete by thin layer chromatography. CH3OH (1 mL) was added and the reaction mixture was stirred for 5 minutes and was washed with 1 M aqueous HCl (3*15 mL) and brine (15 mL), and was dried over sodium sulfate. After filtration, the filtrate was concentrated to provide the title compound, which was used without additional purification. 1H NMR (400 MHz, Chloroform-d) delta ppm 7.60 (dd, J=2.5, 1.2 Hz, 1H), 7.33 (dd, J=8.7, 2.6 Hz, 1H), 6.71 (d, J=8.6 Hz, 1H), 4.74 (d, J=1.0 Hz, 2H), 3.82 (d, J=1.1 Hz, 3H), 0.99 (s, 9H), 0.15 (s, 6H); MS(ESI+) m/z=329.8 (M+H)+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 80866-82-6, 5-Bromo-2-methoxybenzyl alcohol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Couty, Sylvain; De Lemos, Elsa; Desroy, Nicolas; Duthion, Beranger; Gfesser, Gregory A.; Greszler, Stephen N.; Housseman, Christopher Gaetan; Koenig, John R.; Kym, Philip R.; Liu, Bo; Scanio, Marc J.; Searle, Xenia; Wang, Xueqing; Yeung, Ming C.; Zhao, Gang; (263 pag.)US2018/99931; (2018); A1;,
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Synthetic Route of 115-20-8, 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. 115-20-8, name is Trichloroethanol. A new synthetic method of this compound is introduced below.

To a suspension of (2-benzyloxy-3,5-dimethyl) phenoxyacetic acid (270 mg, 0.94 mmol) and 1,3-dicyclohexylcarbodimide (292.0 mg, 1.41 mmol) in CH2Cl2 (10.0 mL) was added pyridine (76.0 mL) and 2,2,2-trichloroethanol (117.0 mL). The suspension was stirred at room temperature for 12 h. The precipitation was filtered through filter paper and the filtrate was concentrated. Flash column (EtOAc in hexanes 5% to 10%) afforded 12c (311.1 mg) in 78.9% yield as an oil. [00783] 1H NMR (CDCl3) ¶7.52-7.28 (m, 5H, C6H5), 6.67 (s, 1H, C6H2), 6.60 (s, 1H, C6H2), 5.04 (s, 2H, CH2C6H5), 4.85 (s, 2H, OCH2CO), 4.84 (s, 2H, OCH2CCl3), 2.26 (s, 3H, CH3C6H2), 2.19 (s, 3H, CH3C6H2); 13C NMR d 167.6, 150.3, 144.4, 137.8, 133.4, 132.5, 128.3, 128.3, 127.8, 125.1, 125.1, 113.1, 94.4. 74.6, 74.0, 65.8, 21.1, 16.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,115-20-8, Trichloroethanol, and friends who are interested can also refer to it.

Reference:
Patent; University of Arkansas; US6657052; (2003); B1;,
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Application of 722-92-9 ,Some common heterocyclic compound, 722-92-9, molecular formula is C9H7F6NO, 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.

Intermcdiate H; 6-Chloro-3-(2-ethoxy-3,4-dioxo-cyclobut- 1 -enylamtno)-2-hydroxy-N-(4-{2,2,2-trif luoro-1 – hydroxy-l-triftuoromepsilonthyl-ethyl)-phenylj-benzenesulfonamide; HIi Preparation of Intermediate Ht; 2-rert-Butyl-6-chloro-ben*zooxazole-7-sul-:onic acid [4-{2,2,2-trifluoro-l -hydroxy-1 -trifluoromethyl-ethy I )~rhohenyl]-amide; 2-tert-Buryl-6-chJoro-ben20oxazole-7-sulfonyl chloride (500 mg, 1.62 mmo.) {prepared according to the procedure described in US 2007/067088 page 17} , 2-(4-aminophenyl)- l,l,l,3,3,3-hexafluoropropan-2-ol (420 mg, 1.62 mmol) and triethylamine (0.226 ml, 1.62 mmol) were combined in THF (5 ml) to give a yellow solution. The reaction, mixture was stirred at room temperature for 2 h then heated at 50 0C for 48 h. The reaction mixture was partitioned between EtOAc (20 ml) and IM HCI (10 ml), live organic layer was washed with brine (10 ml), dried (MgSO-O, filtered and added to silica gel (4 g) then carefully evaporated in vacuo. The silica gel was dry-loaded onto an (Isolure.(TM). Flash Si II 25 g) column for purification by chromatography, eluting with iso-hexane/ErOAc (10/1). The product fractions were combined and evaporated to dryness in vacuo to yield the title product. IH NMR 6H (400MHz DMSO) 8.55 (s, IH), 7.94 (d, IH), 7.61 (d, IH), 7.49 (d, 2H) 7.19 Patent; NOVARTIS AG; BAETTIG, Urs; BRUCE, Ian; PRESS, Neil John; WATSON, Simon James; WO2010/63802; (2010); A1;,
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