Month: November 2020

40800-65-5, 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. 40800-65-5 name is Ethyl 4-amino-3-methylbenzoate, This 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.

1) 4-amino-3-methylbenzoic acid ethyl ester,The di-tert-butyl dicarbonate and absolute ethanol are stirred at 40 to 50 C for 4 to 6 hours to obtain a mixture I.

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; Shenzhen The Second People Hospital; Tan Hui; Li Weiping; Huang Guodong; (8 pag.)CN109761817; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 24398-88-7 as follows. 24398-88-7

[00457] To a stirred solution of 1.3 M LHMDS (25 mL, 32.7 mmol) in THF (10 mL) was added EtOAc (1.9 g, 21.8 mmol) at -78 C under inert atmosphere. After being stirred for 15 min, ethyl- 3-bromo benzoate (5 g, 21.8 mmol) was added and stirring was continued for 2 h; progress of the reaction was monitored by TLC. The reaction was quenched with aq. NH4C1 (10 mL) and extracted with EtOAc (3 x 20 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude product. The crude material was purified by silica gel column chromatography eluting with 4% EtOAc/Hexane to afford compound G (4.5 g, 76.9%) as a mixture with its enolic form as a brown oil. 1H NMR (500 MHz, CDCls): delta 8.07 (s, 1H), 7.86 (d, J= 7.5 Hz, 1H), 7.73-7.69 (m, 1H), 7.37 (t, J= 7.0 Hz, 1H), 4.28-4.26 (m, 2H), 3.92 (s, 2H), 1.24 (t, J= 6.2 Hz, 3H). MS (ESI): m/z 298.8 [M-l].

According to the analysis of related databases, 24398-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; COSFORD, Nicholas David, Peter; DHANYA, Raveendra, Panickar; SHEFFLER, Douglas, J.; WO2015/191630; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

14062-25-0, Adding some certain compound to certain chemical reactions, such as: 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate, 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 14062-25-0.

Ethyl (4-bromophenyl)-acetate (100 g, 411 mmol) Z?-(pinacolato)diboron (125.4 g,493.7 mmol) and potassium acetate (125.4 g, 493.7 mmol) were charged to a 2 L round bottom flask. 1,4-Dioxane (1 L) was added and the mixture was stirred under a nitrogen EPO atmosphere for 15 minutes. [1,1 ‘-Z?w-(Diphenylphosphino)-ferrocene]dichloropalladium(II) CH2Cl2 complex (1:1) (3.36 g, 4.11 mmol) was added and the reaction was heated in an 100 0C oil bath for 2 hours. The reaction was determined complete by analytical HPLC. The solution was concentrated under reduced pressure to remove the dioxane and the residue was dissolved in ethyl acetate. The solution was filtered through a 6 x 4 inch silica gel plug with ethyl acetate (1.5 L) as eluant to give ethyl [4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)- phenylj-acetate (117 g, 98%). 1H NMR (400 MHz, DMSO) delta ppm 7.63 (d, 2H5 J= 8 Hz), 7.27 (d, 2H, J= 8 Hz), 4.07 (q, 2H, J= 7 Hz), 3.68 (s, 2H), 1.28 (s, 12H), 1.16 (t, 3H, J= 7 Hz).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 14062-25-0.

Reference:
Patent; AXYS PHARMACEUTICALS, INC.; WO2006/86609; (2006); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

18595-14-7, A common heterocyclic compound, 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, molecular formula is C9H11NO2, 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.

To a stirred solution of methyl 4-amino-5-methylbenzoate (85) (2.48 g, 15 mmol) in 25 mL of AcOH, NBS (3.0 g, 17 mmol)was added portionwise, the mixture was stirred for 1 h, diluted with water, extracted with DCM, washed with a saturated NaHCO3 solution, dried over a2S04, and rotovapped to yield 3.66 g of methyl 4-amino-3-bromo-5-methylbenzoate (86). XH NMR (CDC13, 400 MHz) delta 8.03 (s, 1H), 7.71 (s, 1H), 4.50 (brs, 2H), 3.87 (s, 3H), 2.25 (s, 3H).

The synthetic route of 18595-14-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IVACHTCHENKO, Alexandre, Vasilievich; ALLA CHEM, LLC; IVASHCHENKO, Andrey, Alexandrovich; SAVCHUK, Nikolay, Filippovich; MITKIN, Oleg, Dmitrievich; (98 pag.)WO2017/39791; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

154825-97-5, 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. 154825-97-5 name is Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, This 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.

To a 50 mL two neck flask were added methyl 2- (4-bromophenyl) -2-methylpropionate (689 mg, 2.68 mmol) , (R) -tert-butyl 3-oxohexahydroimidazo [1, 5-a] pyrazine-7 (1H) -carboxylate (630 mg, 2.61mmol) , Pd2(dba)3(180 mg, 0.19 mmol) , 2-di-tert-butylphosphino-2′, 4′, 6′-triisopropylbiphenyl (550 mg, 1.26 mmol) , Cs2CO3(173 mg, 0.53 mmol) and 1, 4-dioxane (25 mL) , the mixture was stirred at 90 for 12 hours. After the reaction was completed, the mixture was cooled to rt and filtered. The filter cake was washed with EtOAc (25 mL) . To the filtrate were added EtOAc (75 mL) and water (50 mL) , the mixture was shaken and separated into layers. The water layer was extracted with ethyl acetate (50 mL) . The combined organic phases were dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatograph (PE/EtOAc (V/V) = 1.2/1) to give the title compound as a white solid (200 mg, 17.88%) . MS (ESI, pos. ion) m/z: 440.1 [M+Na]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, and friends who are interested can also refer to it.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Xinchang; REN, Qingyun; YAN, Guanghua; GOLDMANN, Siegfried; ZHANG, Yingjun; (253 pag.)WO2019/76310; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

10601-80-6, Adding a certain compound to certain chemical reactions, such as: 10601-80-6, name is Ethyl 3,3-diethoxypropionate, 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 10601-80-6.

Example 22-(6-Chloro-pyridin-2-yl)-pyrimidin-4-ol (Intermediate compound); Ethyl-3,3-diethoxypropionate (1 g, 5.26 ml_) was dissolved in tetrahydrofuran (2 ml_) and aqueous hydrochloric acid (1.5 M) was added. The reaction mixture was stirred at room temperature for 4 hours and extracted with ethyl acetate.The combined organic layers were washed with brine, dried over sodium sulphate, filtrated and evaporated. Ethanol (20 ml_) was added and cooled to 0C.Crude theta-chloro-pyridine^-carboxamidine (560 mg, 1.44 mmol) in water (5 ml_) was added and the reaction mixture was stirred for 15 minutes at 0C. Sodium hydroxide (841 mg, 21.03 mmol) was added followed by additional stirring at room temperature for 20 hours. The reaction mixture was concentrated under reduced pressure. Water was added and extracted with chloroform. The combined organic phases were washed with brine, dried over sodium sulphate filtated and evaporated to give 2-(6-chloro-pyridin-2-yl)-pyrimidin-4-ol (350 mg, 53%) as a brownish solid.

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, Ethyl 3,3-diethoxypropionate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NeuroSearch A/S; WO2008/28935; (2008); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 4897-84-1 name is Methyl 4-bromobutanoate, This 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. 4897-84-1

(III) 4- (4-HYDROXYMETHYL-2-METHOXY-5-NITROPHENOXY) butyric acid allyl ester (52) 50 51 52 4- 4-FORMYL-2-METHOXYPHENOXY)-BUTYRIC ACID methyl ester (48); A solution of vanillin (47) (40.00 g, 262.89 mmol) and methyl-4- bromobutyrate (50.00 g, 276.18 mmol) in DMF (200 ML) was allowed to stir over potassium carbonate (51.53 g, 372.40 mmol) for 16 hours. Water was added to the reaction mixture at which time the product crystallised. The resulting mixture was filtered and dried in vacuo for 16 hours to afford the keto-ester (48) as a white solid (41.3g, 66%). MP = 57-59C. 1H NMR (250 MHz, CDCLG) 6 9.80 (s, 1H), 7.46-7. 40 (m, 2H), 6.97 (d, J = 8.1 Hz, 1H), 4.16 (t, J = 6.3 Hz, 2H), 3.92 (s, 3H), 3.70 (s, 3H), 2.57 (t, J = 7.2 Hz, 2H), 2.20 (pent, J = 6.7 Hz, 2H). 13C NMR (67.8 MHz, CDC13) 188.2 (C1), 173.7 (C12), 153.8 (Cquat. ), 152.0 (Cquat. ), 144.1 (Cquat. ), 125.8 (CMETHINE), 110.3 (C3), 108.5 (C6), 69.0 (C9), 57.0 (C8), 52.2 (C13), 30.6 (CLL), 24.5 (C10). It was decided to adopt the numbering system shown in the figure below for the molecule for ease of peak assignment IN 13C NMR. IR (cm-1) 3450,3332, 2952,1737, 1685,1587, 1467,1407, 1006, 938,864, 813,730, 656. MS (M+) 253. Anal. Calcd for C13 H16 Os : C, 61.90 ; H, 6.39. Found: C, 61.50 ; H, 6.39.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-bromobutanoate, and friends who are interested can also refer to it.

Reference:
Patent; SPIROGEN LIMITED; WO2005/23814; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

18066-68-7, 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. 18066-68-7 name is Ethyl 2-(3,4-dimethoxyphenyl)acetate, This 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.

(ii) 19.3 g (0.19 mol) of dried isopropylamine was dissolved in 100 ml of anhydrous tetrahydrofuran. The solution was cooled to -60 C. or below in a dry ice/acetone bath, and 120 ml of a solution of 1.6M n-butyllithium in n-hexane was dropwise added thereto at this temperature with stirring. The mixture was stirred for 15 min, and a solution of 40.37 g (0.18 mol) of ethyl 3,4-dimethoxyphenylacetate in 200 ml of anhydrous tetrahydrofuran was dropwise added thereto at the same temperature. After stirring for additional 15 min, a solution of 38.45 g (0.18 mol) of 2-chloro-3-methoxy-beta-nitrostyrene in 400 ml of anhydrous tetrahydrofuran was dropwise added thereto with stirring at such a dropping rate that the temperature of the system did not exceed -50 C. After stirring for 30 min, a small amount of water was added thereto and tetrahydrofuran was distilled off to some extent in vacuo. A 6N hydrochloric acid solution was added to the residue for acidification, and the acidified residue was extracted twice with dichloromethane. The resultant organic phase was washed twice with a saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled off in vacuo, and the residue was purified by silica gel column chromatography (eluted with a n-hexane/ethyl acetate mixture in a n-hexane to ethyl acetate ratio of 2:1) to prepare 75.1 g of viscous crude ethyl 3-(2-chloro-3-methoxyphenyl)-2-(3,4-dimethoxyphenyl)-4-nitrobutyrate.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-(3,4-dimethoxyphenyl)acetate, and friends who are interested can also refer to it.

Reference:
Patent; Eisai Co., Ltd.; US5444083; (1995); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common heterocyclic compound, 35180-01-9, name is Chloromethyl isopropyl carbonate, molecular formula is C5H9ClO3, 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. 35180-01-9.

Example 1 2-butyl-4-chloro-1-[2′-(1H-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazole-5-carboxylic acid, 1-[(isopropoxycarbonyl)oxy]methyl ester (compound 1) 2-butyl-4-chloro-1-[2′-(1H-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazole-5-carboxylic acid (prepared by the method disclosed in U.S. Pat. No. 5,138,069) was reacted with trityl chloride to obtain 2-butyl-4-chloro-1-[2′-(1-triphenylmethyl-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazole-5-carboxylic acid. To a 100 ml of one-necked flask, 0.523 g of 2-butyl-4-chloro-1-[2′-(1-triphenylmethyl-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazole-5-carboxylic acid, 0.124 g of potassium carbonate, and 5 ml of N,N-dimethylacetamide were added in turn. The solution was stirred at the room temperature for 20 minutes. Then 0.562 g of 1-chloromethyl isopropyl carbonate was added and the mixture was reacted at 45-50 C. for 16 h. After the reaction was completed, the mixture solution was filtered, and 30 ml of water was added into the filtrate. The resulting mixture was extracted with 30 ml of ethyl acetate twice. The organic phase was dried and concentrated to give 1.724 g of oil, which was directly used in the next reaction without purification. 10 ml of dioxane and 5 ml of 4 mol/L HCl were added, and the resulting mixture was reacted at the room temperature for 16 h. After the reaction was completed, the solution was adjusted to pH 6-7 using aqueous sodium bicarbonate solution. The solution became turbid, and was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried, concentrated to give 0.436 g of 2-butyl-4-chloro-1-[2′-(1H-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazole-5-carboxylic acid, 1-[(isopropoxycarbonyl)oxy]methyl ester. 1H-NMR: (CDCl3) deltaH (ppm): 0.89 (t, 3H, J=14.6), 1.24 (d, 6H, J=6.3), 1.37 (m, 2H, J=22.1), 1.69 (m, 2H, J=30.5), 2.64 (t, 2H, J=15.5), 4.81 (m, 1H, J=12.4), 5.54 (s, 2H), 5.86 (s, 2H), 6.95-7.64 (8H), 8.08 (d, 1H, J=7.42) ESI (+) m/z: 552.7

The synthetic route of Chloromethyl isopropyl carbonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guo, Jianhui; An, Dong; US2009/326024; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

33993-24-7, 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. 33993-24-7, name is Cyclopropanecarboxylic anhydride belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Will contain water (0.32 ml) with trifluoroacetic acid (4.2 ml) cooled to -5 C the solution, and ethyl-N-[(mesitylsulfonyl)oxy]ethaneimidate (2.29 g, 8.02 mmol) blending and the stirring the mixture at room temperature for up to 1 hour. The reaction mixture with ice-water (20 ml) then mixes and with dichloromethane (20 ml) extraction. The sodium sulfate machine in on the drying and filtering, and the obtained solution for the 0 C dropwise to 5-bromo-4-methylpyridin-2-amine (1 g, 1.79 mmol) in dichloromethane (15 ml) in solution. The mixture stirred at room temperature for 1 hour and then with diethyl ether (20 ml) incorporation. The precipitated solid is filtered out of the diethyl ether is used for cleaning. The solid for drying under high vacuum. This produced 1.22 g (theoretical value of 57%) of the 1,2-diamino-5-bromo-4-methylpyridinium-2,4,6-trimethylbenzolsulfonate. The 1,2-diamino-5-bromo-4-methylpyridinium-2,4,6-trimethylbenzolsulfonate (580 mg, 1.44 mmol) and cyclopropylcarboxylic acid anhydride (1.33 g, 8.65 mmol) in pyridine (2.5 ml) in solution in 100 C stirring up to 8 hours. The reaction mixture is concentrated in the rotary evaporator and the residual substance is dissolved in DMSO/water/b in nitrile. By this solution the sealing ripoll filter filtering and by preparative HPLC (eluents: acetonitrile/water with 0.1% trifluoro acetic acid the gradient) to be purified. This generating 279 mg (theoretical value of 69%) the subject compound.

The synthetic route of 33993-24-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROEHN, ULRIKE; ELLERMANN, MANUEL; STRASSBURGER, JULIA; WENDT, ASTRID; ROEHRIG, SUSANNE; WEBSTER, ROBERTALAN; SCHMIDT, MARTINAVICTORIA; TERSTEEGEN, ADRIAN; BEYER, KRISTIN; SCHAEFER, MARTINA; BUCHMUELLER, ANJA; GERDES, CHRISTOPH; SPERZEL, MICHAEL; SANDMANN, STEFFEN; HEITMEIER, STEFAN; HILLISCH, ALEXANDER; ACKERSTAFF, JENS; TERJUNG, CARSTEN; (148 pag.)TW2016/5809; (2016); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics