Tag: M.W=300-400

Application of 169751-72-8 , The common heterocyclic compound, 169751-72-8, name is tert-Butyl 14-hydroxy-3,6,9,12-tetraoxatetradecan-1-oate, molecular formula is C14H28O7, 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.

4-Toluenesulfonyl chloride (2.49 g, 13.1 mmol) was added to an ice-cooled solution of tert- butyl 14-hydroxy-3,6,9,12-tetraoxatetradecan-l-oate (2.96 g, 7.68 mmol) in pyridine (30 mL). The reaction was stirred at room temperature for 5 hours. The reaction mixture was partitioned between ethyl acetate (50 mL) and 2 M aq. HCI (40 mL). The organic extract was separated, washed with 2M aq HCI (40 mL), followed by saturated sodium bicarbonate (50 mL) and brine (50 mL). The organic extract was then dried and concentrated under reduced pressure and the product was purified by chromatography on silica 330g, using a gradient elution from 0-100% methyl tert-butyl ether in cyclohexane to yield tert-butyl 14-(tosyloxy)- 3,6,9,12-tetraoxatetradecan-l-oate (2.17 g, 4.50 mmol, 59 % yield), as a colourless oil. 1H NMR (400 MHz, CDCI3 ) delta ppm 1.47 (s, 9H), 2.45 (s, 3H), 3.58 (s, 4H), 3.63 (m, 4H), 3.68 (m, 8H), 4.01 (s, 2H), 4.16 (m, 2H), 7.34 (d, 2H, J=8.3Hz), 7.78 (d, 2H, J=8.3Hz) . MS (m/z) 463

The synthetic route of 169751-72-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; HARLING, John David; NEIPP, Christopher E.; PENDRAK, Israil; SMITH, Ian Edward David; TERRELL, Lamont Roscoe; YOUNGMAN, Mark; (120 pag.)WO2017/46036; (2017); A1;,
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Synthetic Route of 23377-40-4, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.23377-40-4, name is 3-(Hexadecyloxy)propan-1-ol, molecular formula is C19H40O2, molecular weight is 300.52, as common compound, the synthetic route is as follows.

Compound 315: To a solution of 1H-tetrazole (0.415 g, 5.92 mmol) in 25 ml ether and 10 ml acetonitrile diisopropylamine (0.93 ml, 0.726 g, 7.03 mmol) was added. The precipitate was filtered off, washed with ether and dried under vacuum to give diisopropylammonium tetrazolide.Compound 316: 3-(hexadecyloxy)propan-1-ol (0.301 g, 1.00 mmol) and diisopropylammonium tetrazolide (0.115 g, 0.67 mmol) were coevaporated with DCM-AcCN mixture(10:10) 3 times. Dried mixture was dissolved in 7 ml DCM and added 3- ((bis(diisopropylamino)phosphino)oxy)propanenitrile (0.673 ml, 2.120 mmol). After 1 hour stirring at room temperature 1 ml methanol was added and stirred for 15 minutes. Then reaction was concentrated under vacuum; diluted with 10%TEA solution in EtOAc (100 ml) and washed with 10%NaHCO3 solution (2 x 50 ml) and water (2 x 50 ml); dried over anhydrous MgSO4; filtered off and evaporated. The crude product was purified with column chromatography using Hexanes:EtOAc:TEA (10:4:0.5). 1H-NMR: 3.89-3.54 (m, 6H); 3.49 (t, 2H, J=6.4 Hz); 3.39 (t, 2H, J=6.4Hz); 2.63 (dt, 2H, J=1.6, 6.4 Hz); 1.89-1.83 (m, 1H); 1.57-1.51 (m, 1H); 1.24 (s, 24H); 1.19-1.16 (m, 16H); 0.87 (t, 3H, J=6.4 Hz).

The chemical industry reduces the impact on the environment during synthesis 23377-40-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; EMORY UNIVERSITY; LIOTTA, Dennis, C.; PAINTER, George, R.; BLUEMLING, Gregory, R.; DE LA ROSA, Abel; (408 pag.)WO2016/145142; (2016); 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. 647-42-7, name is 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctan-1-ol. A new synthetic method of this compound is introduced below., category: alcohols-buliding-blocks

To a mixture, kept under stirring, of C6F13CH2CH2OH(252 g, 0.692 moles), tetrahydrofurane (350 ml) and cyclohexane (300 ml) at 250C, an aqueous solution ofNaOH (400 ml, 50%) was added drop-wise. After stirring for 2 hours, benzyltriethyl ammonium chloride (25 g, 0.11 moles) as phase transfer catalyst, and then 1- bromopentane (209 g, 1.38 moles) were added. The reaction mixture was kept under stirring at 400C for 40 hours, then at 700C for 8 hours. The resulting mixture was poured into water and the organic phase thus ob- tained was washed two times with water. After removing the fraction having a low boiling point, the raw product was subjected to distillation at reduced pressure, thus obtaining 215 g of C6F13CH2CH2O (CH2) 4CH3 (yield 72%, boiling point 110C/6 mbar, n 1.3385) . Spectrographic data confirm the obtained structure: GC/MS m/z at 435 (M+H)+, 377 (M-CH2CH2CH2CH3) +, 71 (- CH2CH2CH2CH2CH3) + ; for NMR data see Tables 1-2.

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, 647-42-7, 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctan-1-ol.

Reference:
Patent; ALChiMI.A. S.r.l.; WO2009/133575; (2009); A1;,
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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. 24131-31-5, name is (3,5-Bis(benzyloxy)phenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows. category: alcohols-buliding-blocks

Phosphorus tribromide was added to the CH2Cl2 solution (10 mL) of [3,5-bis(benzyloxy)phenyl]methanol (11, 0.008 mol) at 0 C for 2 h. Ice water was added to reaction solution, and extracted with diethyl ether. The crude product was evaporated and purified by silica-gel chromatography using petroleum/ethyl acetate 15:1 as an eluent to give bromide 12 (0.0028 mol, 35%). 1H-NMR (DMSO-d6, 300 MHz) delta: 7.11-7.43 (10H), 6.65 (2H, d, J = 2.1 Hz), 6.55 (1H, s), 5.03 (4H, br s), 4.35 (2H, s). HPLC analysis 96.9% (MeOH: H2O = 85: 15 (V/V), tR = 8.67 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, 24131-31-5, (3,5-Bis(benzyloxy)phenyl)methanol.

Reference:
Article; Wan, Xiang; Wang, Xiao-Bing; Yang, Ming-Hua; Wang, Jun-Song; Kong, Ling-Yi; Bioorganic and Medicinal Chemistry; vol. 19; 17; (2011); p. 5085 – 5092;,
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With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.647-42-7, name is 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctan-1-ol, molecular formula is C8H5F13O, molecular weight is 364.1, as common compound, the synthetic route is as follows.Computed Properties of C8H5F13O

The same fluoroalkyloxy alkanes as in Examples 1- 4 were prepared following an alternative procedure. A mixture comprising 0.1 moles of fluorinated alcohol, 60 ml of N-methyl-2-pyrrolidone, 0.2 moles of 1- bromoalkane, and 60 ml of a 45% aqueous solution of KOH was heated under stirring for 5 hours at 500C, then at 700C for 2 hours so as to complete the reac- tion. The raw reaction mixture was filtered so as to remove the formed KBr, and then diluted in 20 ml of water; the organic phase thus obtained comprised the desired fluoroalkyloxy alkane (yield: 80%) .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,647-42-7, 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; ALChiMI.A. S.r.l.; WO2009/133575; (2009); A1;,
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Synthetic Route of 10213-78-2, Adding some certain compound to certain chemical reactions, such as: 10213-78-2, name is 2,2′-(Octadecylazanediyl)diethanol,molecular formula is C22H47NO2, 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 10213-78-2.

EXAMPLE V Preparation of Methylbis(2-hydroxyethyl)octadecyl Ammonium Methyl Sulfate in Polyoxyethylene(5)glycoloctadecanoate To 150 g (0.418 gmol) of bis(2-hydroxyethyl)octadecylamine in 203 g of polyoxyethylene(5)glycoloctadecanoate heated to 75 C. with stirring in a 1-liter, 3-neck glass round-bottom flask fitted with a thermometer and electric heating mantle there was added 51.1 g (0.405 gmol) of dimethyl sulfate (Aldrich, 99%). The temperature rose immediately to 120 C.; the heat was removed and the reaction mixture allowed to cool to 35-40 C. at which solidification began to occur. A sample of the mixture analyzed as 48% quaternary, 2.16% amine methylsulfate and 1.67% amine and amine soap, calculated as amine.

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. 10213-78-2, 2,2′-(Octadecylazanediyl)diethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Akzona Incorporated; US4237064; (1980); A;,
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Adding a certain compound to certain chemical reactions, such as: 23377-40-4, 3-(Hexadecyloxy)propan-1-ol, 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, COA of Formula: C19H40O2, blongs to alcohols-buliding-blocks compound. COA of Formula: C19H40O2

Example 6 Hexadecyloxypropyl-2′,3′-isopropylideneuridin-5′-yl-vinyphosphonate TPSCl (5.54 g, 18.3 mmol) is added to the mixture of vinylphosphonic acid from the example 1 (1.8 g, 6.1 mmol), hexadecyloxypropanol (1.45 g, 3.05 mmol), and 1-methylimidazole (1.45 ml, 18.3 mmol) in DCM (60 ml). The reaction mixture is stirred overnight at rt, then extracted/washed with saturated solution of NaHCO3 (2 x 100 ml), 3% aqueous citric acid (2 x 100 ml) and dried over Na2SO4. The organic phase is concentrated in vacuo and the product is obtained by flash chromatography on silica gel using linear gradient of ethanol in chloroform in 71% yield (1.42 g, 2.16 mmol) in the form of colorless wax. A mixture of diastereoisomers ~ 1:1 1H NMR (500.0 MHz, CDCl3): 0.88 (m, 6H, CH3(CH2)15); 1.23-1.33 (m, 52H, CH3(CH2)13CH2CH2-O); 1.348, 1.352 (2 * q, 2 * 3H, 4J= 0.6, (CH3)2C); 1.54 (m, 4H, CH3(CH2)13CH2CH2O); 1.57 (s, 6H, (CH3)2C); 1.92, 1.94 (2 * p, 2 * 2H, Jvic = 6.1, OCH2CH2CH2OC16H33); 3.38, 3.39 (2 * t, 2 * 2H, Jvic, = 6.7, CH3(CH2)13CH2CH2O); 3.48, 3.49 (2 * t, 2 * 2H, Jvic = 6.1, OCH2CH2CH2OC16H33); 4.13, 4.15 (2 * td, 2 * 2H, Jvic = 6.1, JH,P = 4.8, OCH2CH2CH2OC16H33); 4.20-4.30 (m, 4H, H-5′); 4.34-4.38 (m, 2H, H-4′); 4.85, 4.86 (2 * dd, 2 * 1H, J3′,2′ = 6.5, J3′,4′ = 3.6, H-3′); 4.92 (dd, 2H, J2′,3′ = 6.5, J2′,1′ = 2.3, H-2′); 5.700, 5.704 (2 * d, 2 * 1H, J5,6 = 8.1 H-5); 5.74, 5.76 (2 * d, 2 * 1H, J1′,2′ = 2.3, H-1′); 6.03, 6.05 (2 * ddd, 2 * 1H, JH,P = 22.9, Jtrans = 18.4, Jcis = 12.7, =CHP); 6.16, 6.18 (2 * ddd, 2 * 1H, JH,P = 51.8, Jcis = 12.7, Jgem = 1.9, CHcisHtrans=CHP); 6.33, 6.35 (2 * ddd, 2 * 1H, JH,P = 25.5, Jtrans = 18.4, Jgem = 1.9, CHcisHtrans=CHP); 7.34, 7.39 (2 * d, 2 * 1H, J6,5 = 8.1, H-6). 13C NMR (125.7 MHz, CDCl3): 14.07 (CH3(CH2)15); 22.62 (CH3(CH2)13CH2CH2O); 25.19, 25.21 ((CH3)2C); 26.08 (CH3(CH2)14CH2O); 27.04, 27.06 ((CH3)2C); 29.29, 29.45, 29.55, 29.57, 29.58, 29.63 (CH3(CH2)14CH2O); 30.66, 30.68 (d, JC,P = 6.4, OCH2CH2CH2OC16H33); 31.85 (CH3(CH2)13CH2CH2O); 63.56 63.57 (d, JC,P = 5.5, OCH2CH2CH2OC16H33); 64.92, 65.01 (d, JC,P = 5.5, CH2-5′); 66.32, 66.36 (OCH2CH2CH2OC16H33); 71.15, 71.16 (CH3(CH2)14CH2O); 80.60, 80.67 (CH-3′); 84.44, 84.53 (CH-2′); 85.38, 85.62 (d, JC,P = 7.1, CH-4′); 93.82, 94.12 (CH-1′); 102.57, 102.64 (CH-5); 114.42, 114.46 (C(CH3)2); 124.75, 124.80 (d, JC,P = 184.0, =CHP); 136.75, 136.77 (d, JC,P = 1.9, CH2=CHP); 141.43, 141.48 (CH-6); 150.16 (C-2); 163.29, 163.32 (C-4). 31P NMR (202.3 MHz, CDCl3): 18.64, 18.80. IR vmax(KBr) 2925 (vs), 2854 (s), 1709 9vs, sh), 1696 (vs), 1630 (w), 1459 (m), 1421 (m), 1400 (w, sh), 1381 (m), 1270 (m, sh), 1250 (m, sh), 1109 (s), 1078 (s), 1028 (s), 1012 (s), 972 (m, sh), 859 (m), 762 (w), 548 (w), 514 (w) cm-1. HR-ESI C33H58O9N2P (M+H)+ calcd 657.3874; found 657.3876

The synthetic route of 23377-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ustav Organicke Chemie A Biochemie Av Cr, V.v.i.; Mikrobiologicky Ustav AV CR V.V.I.; Ustav Molekularni Genetiky Av Cr, V.v.i.; Trios, spol. s r.o.; EP2527351; (2012); A1;,
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Related Products of 59101-28-9, 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. 59101-28-9, name is 16-Bromohexadecan-1-ol, molecular formula is C16H33BrO, 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.

4.3 Diethyl2-acetamido-2-(i 6-hydroxyhexadecyl)malonate10221] The bromide 15(0.967 g, 2.70 mmol), diethyl 2-ac- etamidomalonate 1 (0.640 g, 2.8 mmol, 1.0 eq.) (obtained as in example 1.1 above) and caesium carbonate (1.680 g, 5.17 mmol, 1.9 eq.) were suspended in acetonitrile (20 mE) and refluxed for 5 h. The mixture was adsorbed at silica gel (1-2 g) and purified by colunm chromatography (silica gel, 1 6.5×4 cm, cyclohexane/ethyl acetate, 4:i)to give a yellowish solid. Yield: 0.912 g (74%).10222] M.p.: 48 C.10223] ?R-NMR (300 MHz, CDC13) oe [ppm]: 1.23-1.63(m, 34R, 5-CR2 to 18-CR2, 23-CR3, 25-CR3), 2.04 (m, 4R,21-CR3, 19-OR), 2.30 (m, 2R, 4-CR2), 3.63 (t, 3J,y=6.6 Rz,2R, 19-CR2), 4.20 (m, 4R, 22-CR2, 24-CR2), 6.84 (s, 1R,2-NR).10224] ?3C-NMR (75 MRz, CDC13) oe [ppm]: 14.0 (q, C-23,C-25), 23.1 (q, C-21), 23.6 (t, C-5), 25.8 (t, C-17), 28.4,29.3,29.7 (t, C-6 to C-16), 32.1 (t, C-18), 32.8 (t, C-4), 62.5 (t,C-22, C-24), 63.0 (t, C-19), 66.6 (s, C-2), 168.3 (s, C-i, C-3),169.0 (s, C-20).10225] Exact mass (ESI): C25R47NO5+Na: calcd. 480.3296, found 480.3300; (C25R47NO5)2+Na: calcd. 937.6699,found 937.6713.

According to the analysis of related databases, 59101-28-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WESTFAELISCHE WILHELMS-UNIVERSITAET MUENSTER; Haufe, Guenter; Levkau, Bodo; Schaefers, Michael; Schilson, Stefani Silke; Keul, Petra; US2014/170067; (2014); 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. 59101-28-9, name is 16-Bromohexadecan-1-ol. A new synthetic method of this compound is introduced below., SDS of cas: 59101-28-9

To a solution of 16-bromohexadecarboxylic acid (10.00 g, 30.0 mmol) in 80 ml THF was added BH3 (70 ml, 70mmol, 1 M in THF) slowly at 0 C. After addition, the reaction mixture was stirred at room temperature for 60-90 minute.The mixture was cooled to 0 C and 80 mL water was added. The aqueous layer was extracted with hexanes (2x100mL). The combined organic layer was washed by 100 mL water, dried with sodium sulfate and concentrated to give awhite solid. The solid was dissolved into). To a solution of this while solid in 100 mL DMF was added potassium thioacetateat room temperature. After stirring at room temperature for 60 -90 minutes, 150 mL ethyl acetate was added to thereaction mixture, followed by 450 mL hexanes and 50 mL water. After being washed by three portions of water, theorganic layer was dried over sodium sulfate and concentrated.. After column chromatography on silica gel (silica gel:(200 g; eluting solvents: 5% ethyl acetate in hexanes; 15% ethyl acetate in hexanes; 25% ethyl acetate in hexanes),K133 was obtained as a white solid. 1H NMR (300 MHz, DMSO-d6) delta 4.31 (t, J=5.1Hz, 1 H, OH),3.37 (t, J=5.1Hz, 2H,CH2OH), 2.81 (t, J=6.9Hz, 2H, SCH2), 2.31 (s, 3H, CH3COS), 1.50 (m, 2H, CH2CH2OH), 1.40 (m, 2H, CH2CH2S), 1.23(br s, 24H, CH2).

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, 59101-28-9, 16-Bromohexadecan-1-ol.

Reference:
Patent; Clinical Micro Sensors, Inc.; CHUNLIN, Tao; EP2220102; (2014); B1;,
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Related Products of 23377-40-4 ,Some common heterocyclic compound, 23377-40-4, molecular formula is C19H40O2, 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 12 Ethyl 3-(hexadecyloxy)propyl {3-[({4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7- yl}methyl)amino]propyl}phosphonate (65), Scheme 12Scheme 12 (3-{[(Benzyloxy)carbonyl]amino}propyl)(ethoxy)phosphinic acid (56) (0.52 g) is evaporated twice with MeCN then dissolved in dry DCM (5 mL) and dry DMF (5 pL). This solution is then added to oxalyl chloride (574 muIota, 5 eq.) in dry DCM (5 mL) under Ar, stirred at room temperature for 2 h and then evaporated twice from dry DCM. The resulting crude phosphonyl chloride (57) in dry DCM (5 mL) is added to a solution of 3- hexadecyloxypropan-1-ol (504 mg, 1.3 eq.) and dry pyridine (1 mL) in dry DCM (3 mL). The mixture is stirred at room temperature for 3 h and then treated with saturated sodium bicarbonate solution, extracted with DCM, dried and evaporated. Flash chromatography (hexanes- EtOAc, followed by 5% v/v MeOH in EtOAc) gives benzyl N-(3-{ethoxy[3- (hexadecyloxy)propoxy]phosphoryl}propyl)carbamate (62) (110 mg). 1H NMR (500 MHz, CDCI3) delta 7.36-7.26 (m, 5H), 5.09 (s, 2H), 4.12-4.08 (m, 2H), 3.49-3.47 (m, 2H), 3.40-3.37 (m, 2H), 3.32-3.25 (m, 2H), 1.92-1.89 (m, 2H), 1.79-1.75 (m, 2H), 1.58-1.54 (m, 2H), 1.32-1.25 (m, 30H), 0.89-0.87(m, 3H). 3C NMR (125MHz, CDCI3) delta 156.4,136.6,128.5, 128.1 , 71.2, 66.6, 62.9, 61.7, 31.9, 30.9, 29.7, 29.5, 29.3, 26.2, 22.7, 16.4, 14.1. 31P NMR (202 MHz, CDCI3 ) delta 31.7. ESI-HRMS for C32H58N06PNa [M+Na]+ calcd 606.3899; found 686.3904.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,23377-40-4, its application will become more common.

Reference:
Patent; INDUSTRIAL RESEARCH LIMITED; ALBERT EINSTEIN COLLEGE OF MEDICINE OF YESHIVA UNIVERSITY; CLINCH, Keith; CRUMP, Douglas Ronald; EVANS, Gary Brian; HAZLETON, Keith Zachary; MASON, Jennifer Mary; SCHRAMM, Vern L.; TYLER, Peter Charles; WO2012/150866; (2012); A1;,
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