Author: tianli

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.30379-58-9, name is Benzyl 2-hydroxyacetate, molecular formula is C9H10O3, molecular weight is 166.17, as common compound, the synthetic route is as follows.Quality Control of Benzyl 2-hydroxyacetate

2-(Fluorenylmethoxycarbonyl)hydroxyacetic acid benzyl ester (657). To a solution of benzyl glycolate (6.0 g, 36.1 mmol) in CH2Cl2, cooled via ice-water bath, was added fluorenylmethoxy chloroformate (14 g, 1.5 equiv.) then diisopropylethylamine (9 mLs, 1.5 equiv.). After 1 hour, reaction mixture was poured into a saturated aqueaous solution of ammonium chloride and extracted with CH2Cl2, dried over Na2SO4 then concentrated in vacuo. The product was triturated from MeOH to obtain 2.2 g of 657 as a first crop of white solid. 2-(Fluorenylmethoxycarbonate) acetic acid (658). To a solution of 657 (2.2 g, 5.93 mmol) in tetrahydrofuran was added 5% Pd/C (220 mg). The resulting suspension was vigorously stirred under hydrogen atmosphere. After 90 min, the reaction mixture was filterred through Celite. The filtrate was poured into saturated aqueous NaHCO3 and washed twice with EtOAc. The aqueous layer was then acidified and the product extracted twice with CH2Cl2, dried over Na2SO4 and concentrated in vacuo to afford 1.46 g (88%) of 658 as a white solid. 2-(Fluorenylmethoxycarbonate) acetyl chloride (659), was prepared from 658 by the method used to prepare 643 to afford 659 as a crude product. (3S)-3-[(3S)-2-Oxo-3-(3,5-dichloro-4-hydroxybenzoyl)amino-5-(2-fluorenylmethoxycarbonate)acetyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetylamino]4-oxo-butyric acid tert-butyl ester semicarbazone (660), was synthesised from 600b, using 659, by methods used to prepare 604d from 600b to afford 453 mg of 660. (3S)-3-[(3S)-2-Oxo-3-(3,5-dichloro-4-hydroxybenzoyl)amino-5-(2-hydroxy)acetyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetylamino]4-oxo-butyric acid tert-butyl ester semicarbazone (661). A solution of 660 (423 mg) in MeOH:Et2NH (1:1, v/v) was stirred at ambient temperature.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,30379-58-9, Benzyl 2-hydroxyacetate, and friends who are interested can also refer to it.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; US6204261; (2001); B1;,
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Application of 3597-91-9, Adding some certain compound to certain chemical reactions, such as: 3597-91-9, name is [1,1′-Biphenyl]-4-ylmethanol,molecular formula is C13H12O, 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 3597-91-9.

A mixture of K2CO3 (1 mmol) and the catalyst (52 mg, ?3 mol% of Pd2+) in toluene (5 ml) was prepared in a two necked flask. The flask was evacuated and refilled with pure oxygen. To this solution, the alcohol (1 mmol, in 1 ml toluene) was injected and the resulting mixture was stirred at 80 C under an oxygen atmosphere. After completion of reaction, the reaction mixture was filtered off and the catalyst rinsed twice with CH2Cl2 (5 ml). The excess of solvent was removed under reduced pressure to give the corresponding carbonyl compounds.

According to the analysis of related databases, 3597-91-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Alizadeh; Khodaei; Kordestania; Beygzadeh; Journal of Molecular Catalysis A: Chemical; vol. 372; (2013); p. 167 – 174;,
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Synthetic Route of 63012-03-3, 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. 63012-03-3, name is (3-Chlorophenyl)(phenyl)methanol. A new synthetic method of this compound is introduced below.

To the mixture of (3-chlorophenyl)(phenyl)methanol (42.6 mg, 0.195 mmol), (cyanomethyl)trimethylphosphonium iodide (63.2 mg, 0.26 mmol) and 8-((2S,5R)-2,5- dimethylpiperazin-1-yl)-5-methyl-6-oxo-5,6-dihydro-1,5-naphthyridine-2-carbonitrile, TFA (44.6 mg, 60 %wt, 0.065 mmol) in propanenitrile (0.3 mL) was added Hunig?s base (0.114 mL, 0.65 mmol). The reaction mixture was stirred at 110 C for 5 hours. The crude material was purified via preparative LC/MS with the following conditions: (1934) Column: XBridge C18, 200 mm x 19 mm, 5 mm particles; Mobile Phase A: 5:95 acetonitrile: water with 10 mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10 mM ammonium acetate; Gradient: a 0 minute hold at 50 % B, 50-90 % B over 20 minutes, then a 4 minute hold at 100 % B; Flow Rate: 20 mL/min; Column Temperature: 25 C. Fraction collection was triggered by MS and UV signals. Fractions containing the product were combined and dried via centrifugal evaporation. The yield of diastereomeric product was 7.4 mg. Calculated molecular weight 498.03. Analytical LC/MS was used to determine the final purity. Injection 1 conditions: Column: Waters XBridge C18, 2.1 mm x 50 mm, 1.7 mm particles; Mobile Phase A: 5:95 (1935) acetonitrile:water with 10 mM ammonium acetate; Mobile Phase B: 95:5 (1936) acetonitrile:water with 10 mM ammonium acetate; Temperature: 50 C; Gradient: 0 %B to 100 %B over 3 min, then a 0.50 min hold at 100 %B; Flow: 1 mL/min; Detection: MS and UV (220 nm). Injection 1 results: Purity: 99.4 %; Observed Mass: 498.12; Retention Time: 2.74 min. Injection 2 conditions: Column: Waters XBridge C18, 2.1 mm x 50 mm, 1.7 mm particles; Mobile Phase A: 5:95 acetonitrile:water with 0.1 % trifluoroacetic acid; Mobile Phase B: 95:5 acetonitrile:water with 0.1% trifluoroacetic acid; Temperature: 50 C; Gradient: 0 %B to 100 %B over 3 min, then a 0.50 min hold at 100 %B; Flow: 1 mL/min; Detection: MS and UV (220 nm). Injection 2 results: Purity: 98.1 %; Observed Mass: 498.13; Retention Time: 1.83 min

At the same time, in my other blogs, there are other synthetic methods of this type of compound,63012-03-3, (3-Chlorophenyl)(phenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; CHUPAK, Louis S.; DARNE, Chetan Padmakar; DING, Min; GENTLES, Robert G.; HUANG, Yazhong; KAMBLE, Manjunatha Narayana Rao; MARTIN, Scott W.; MANNOORI, Raju; MCDONALD, Ivar M.; OLSON, Richard E.; RAHAMAN, Hasibur; JALAGAM, Prasada Rao; ROY, Saumya; TONUKUNURU, Gopikishan; VELAIAH, Sivasudar; WARRIER, Jayakumar Sankara; ZHENG, Xiaofan; TOKARSKI, John S.; DASGUPTA, Bireshwar; REDDY, Kotha Rathnakar; RAJA, Thiruvenkadam; (0 pag.)WO2020/6018; (2020); A1;,
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Electric Literature of 75476-86-7, 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 75476-86-7 as follows.

A mixture of 15A (11 g, 51.6 mmol) and Ph3P-HBr (17.7 g, 51.6 mmol) in benzene (35 ml_) was heated at 90 9C overnight. After cooling to RT, the solid was filtered and dried in vacuo. The solid was washed with Et2O and acetone, and then vacuum dried to afford 15B (18.9 g, 68%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75476-86-7, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; WO2008/100480; (2008); A1;,
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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 148043-73-6, Adding some certain compound to certain chemical reactions, such as: 148043-73-6, name is 4,4,5,5,5-Pentafluoropentan-1-ol,molecular formula is C5H7F5O, 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 148043-73-6.

EXAMPLE 1 Into a 1L hastelloy C autoclave, pentafluoropentanol (C2F5(CH2)3OH, 519 g) and trifluoromethane sulfonic acid (20 g) were charged and stirred at 175C for 14 hours. The reactor pressure at that time was 0.7 MPa (gage pressure). After the reaction, the obtained crude liquid was subjected to liquid separation, and the organic phase was washed twice with water (50 ml) and dried over magnesium sulfate, followed by filtration to obtain a crude liquid. The conversion by the reaction was 75.7% as measured by gas chromatography (hereinafter referred to simply as GC). By distillation under reduced pressure, the desired following compound (I-1) (172 g) was obtained as a fraction of (60 to 61C)/1.4 kPa (absolute pressure). The GC purity was 99.9%. By the NMR analysis, formation of the following compound (I-1) was confirmed. Compound (I-1) : C2F5(CH2)3O(CH2)3C2F5.1HNMR (300.4MHz, CDCl3, TMS) delta (ppm) : 1.87 (m, 2H), 2.12 (m, 2H), 3.48 (m, 2H).19FNMR (282.7MHz, CDCl3, CFCl3) delta (ppm) : -86.1 (3F), -118.8(2F).

According to the analysis of related databases, 148043-73-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASAHI GLASS COMPANY LTD.; EP1577284; (2005); A1;,
Alcohol – Wikipedia,
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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.96-35-5, name is Methyl 2-hydroxyacetate, molecular formula is C3H6O3, molecular weight is 90.08, as common compound, the synthetic route is as follows.SDS of cas: 96-35-5

Intermediate 4: 4-oxotetrahydrofuran-3-carbonitrile [00211] To a solution of potassium tert-butoxide (24.91g, 222.O3mmol) in THF (200mL) at 0Cwas added methyl glycolate (20.OOmL, 259mmo1) dropwise. The mixture was left to stir for 10 minutes before adding acrylonitrile (14.62mL, 222mmo1) dropwise. The reaction then allowed to warm to room temperature and left to stir for 3 hours. Water and EtOAc were added to the reaction mixture and the layers separated. The aqueous layer as then acidified to pHi with 1 M HCI and extracted twice with EtOAc. The combined organic layers were then washed with brine, dried over Na2SO4 and then passed through a hydrophobic frit before being concentrated under reducedpressure to afford 4-oxotetrahydrofuran-3-carbonitrile (10.29g, 93mmol, 42% yield) as a yellow solid.1H NMR (CDCI3, 400MHz) O/ppm: 4.65 (1H, t, J= 9.3Hz), 4.26 (1H, t, J= 9.3Hz), 4.18 (1H, d, J=17.5Hz), 4.02 (1H, d, J= 17.5Hz), 3.61 (1H, t, J= 9.3Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,96-35-5, Methyl 2-hydroxyacetate, and friends who are interested can also refer to it.

Reference:
Patent; REDX PHARMA PLC; ARMER, Richard; BELFIELD, Andrew; BINGHAM, Matilda; JOHNSON, Alice; MARGATHE, Jean-Francois; AVERY, Craig; HUGHES, Shaun; MORRISON, Angus; (278 pag.)WO2016/51193; (2016); A1;,
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Synthetic Route of 111-90-0, 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 111-90-0 as follows.

EXAMPLE 6 11.2 g (0.083 mole) of diethylene glycol monoethyl ether was added dropwise to a mixture consisting of 1.6 g (0.042 mole) of sodium borohydride, 10 ml of xylene and 5 g (0.027 mole) of methyl caprate at 90 C. over two hours while agitating the mixture. Subsequently, the mixture was agitated at the same temperature for 2.5 hours. After cooling to room temperature, the mixture was neutralized with dilute sulfuric acid. As a result, n-decanol was obtained in 97% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,111-90-0, its application will become more common.

Reference:
Patent; Kao Corporation; US5196601; (1993); 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. 20712-12-3, name is (2-Amino-5-bromophenyl)methanol, molecular formula is C7H8BrNO, 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. category: alcohols-buliding-blocks

Synthesis of 6-bromo-2-(3,5-dimethylphenyl)quinoline(2-Amino-5-bromophenyl)methanol (22 g, 109 mmol), 3,5-dimethylacetophenone (24.2 g, 163 mmol), RuCl2(PPh3)3 (1.05 g, 1.09 mmol), KOH (11.0 g, 196 mmol) were refluxed in 270 mL of toluene for 18 h.Water was collected from the reaction using a Dean-stark trap.The reaction mixture was allowed to cool to room temperature and filtered through a silica gel plug and eluted with 5percent ethyl acetate in hexanes.The product was further purified by Kugelrohr distillation and crystallization from methanol.

With the rapid development of chemical substances, we look forward to future research findings about 20712-12-3.

Reference:
Patent; Universal Display Corporation; US2012/217868; (2012); A1;,
Alcohol – Wikipedia,
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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.495-76-1, name is Benzo[d][1,3]dioxol-5-ylmethanol, molecular formula is C8H8O3, molecular weight is 152.1473, as common compound, the synthetic route is as follows.category: alcohols-buliding-blocks

General procedure: To a solution of Cu(OAc)2 (0.025 mmol, 0.0046 g) and potassium tert-butoxide (0.175 g, 2.5 mmol) in anhydrous dioxane (3 mL), the corresponding amine 1 (2.5 mmol) or the triphenylphosphoranylidenaniline 18 (2.5 mmol) and the correspondent alcohol 2 or 4 (3.75 mmol) were added successively under inert argon atmosphere. After 2 or 5 days of reaction at 130 C (see Table 2 and Scheme 2), the resulting mixture was hydrolyzed with a saturated solution of ammonium chloride (10 mL). The mixture was extracted with AcOEt (3×10 mL) and washed with brine (10 mL), after drying with anhydrous MgSO4, was filtered on Celite and the solvents were removed under low pressure(15-18 Torr). The resulting mixture was purified by column chromatography (if needed).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,495-76-1, Benzo[d][1,3]dioxol-5-ylmethanol, and friends who are interested can also refer to it.

Reference:
Article; Martinez-Asencio, Ana; Ramon, Diego J.; Yus, Miguel; Tetrahedron; vol. 67; 17; (2011); p. 3140 – 3149;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts