Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 13195-64-7, name is Diisopropyl malonate, 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 13195-64-7, HPLC of Formula: C9H16O4

(1) using 830 mmol of sodium hydride as a catalyst,200 mmol of diisopropyl malonate with 440 mmolPropargyl bromide was added to 210 mL of anhydrous acetonitrile in an ice water bath.Stir the reaction for 8 hours.The product was washed with water, extracted with EtOAc EtOAc.Obtaining the product, compound 1;

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, Diisopropyl malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Anhui Normal University; Zheng Xiaojie; Hu Yimin; (15 pag.)CN108947828; (2018); A;,
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Reference of 2065-23-8, 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. 2065-23-8 name is Methyl 2-phenoxyacetate, 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.

Methyl phenoxyacetate (99.9 g, 0.6 mol) was added dropwise to [CHLOROSULFONIC] acid (279.6 g, 159.5 mL, 2.4 mol) at-5 C at such a rate to maintain internal temperature between 0 to-5 C (addition took about 60 min). Some solid formed during this addition. The cooling bath was removed and the reaction mixture was stirred at room temperature for an additional 1.5 hr. The reaction mixture was poured into a vigorously stirring mixture of dichloromethane (900 mL) and methanol (100 [ML)] at [0 C.] After 15 min the cooling bath was removed and the resulting mixture was stirred at room temperature for 1 hr. The resulting mixture was washed with ice cold water (2 X 250 mL). The combined aqueous layers were back extracted with dichloromethane [(1] X 250 mL). The combined organic layers were washed with brine [(1 X] 200 mL), dried over anhydrous magnesium sulfate (15 g) and concentrated under reduced pressure to give 132 g (83%) of the title compound as a white solid.’H NMR [(60MHZ)] [(CDC13)] 8 8.2-7. 2 (AB, 4H), 4.95 (s, 2H), 3.95 (s, 3H).

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

Reference:
Patent; GARST, Michael, E.; SACHS, George; SHIN, Jai, Moo; WO2004/9583; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 63485-50-7, name is cis-Methyl 3-hydroxycyclobutanecarboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C6H10O3

cis-3-hydroxycyclobutylcarboxylic acid methyl ester (2730 g, 21.0 mol, 1.0 eq) prepared in Example 1 was dissolved in tetrahydrofuran (30 L) and cooled to -10 C.p-Nitrobenzoic acid (4178 g, 25.0 mol, 1.2 eq.), diethyl azodicarboxylate (4354 g, 25.0 mol, 1.2 eq.), triphenylphosphine (6557 g, 25.0 mol, 1.2 eq.).It was then stirred at room temperature for 16 h under nitrogen.The reaction was complete by TLC, the tetrahydrofuran was removed, and methyl t-butyl ether (20 L) was added and stirred for 0.5-1 h.Filter and filter cake was washed twice with methyl tert-butyl ether.All filtrates were collected and the filtrate was washed with saturated aqueous sodium bicarbonate.Dispense, dry and concentrate.The crude product was then beaten with a mixed solvent of ethyl acetate/petroleum ether, filtered and concentrated to give a pale yellow powder.Trans-III compound trans-p-nitrobenzoic acid (3-methoxycarbonylcyclobutyl) ester (4468 g, 16.0 mol), yield 76%, purity 95%.

The synthetic route of 63485-50-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Bide Pharmaceutical Technology Co., Ltd.; Xiong Shichuan; Mi Taoran; Fan Jianjian; Zhang Ruihao; (9 pag.)CN108129288; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 85953-29-3, name is Methyl 2-chloro-4-fluorobenzoate, 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. Recommanded Product: 85953-29-3

2-Chloro-4-fluoro-benzoic acid methyl ester (500 mg, 2.65 mmol) and 4-bromophenol (504 mg, 2.9131 mmol) were sequentially added to the dry reaction flask.Potassium carbonate (731 mg, 5.2971 mmol), DMAc (5 mL), protected by a nitrogen balloonThe reaction was heated to 120 C for 12 h, cooled to rt then water (20 mL) and ethyl acetate (20 mL). The aqueous phase was added with 1 M hydrochloric acid, and the pH was adjusted to 3-4, then ethyl acetate (15 mL) was added to precipitate a white solid and filtered.The filter cake was washed with ethyl acetate (5 mL).The title compound is a white solid(230 mg, 27%).

The synthetic route of Methyl 2-chloro-4-fluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Liu Xinchang; Huang Jianzhou; Zhang Yingjun; S ¡¤geerdeman; (267 pag.)CN109111451; (2019); A;,
Ester – Wikipedia,
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Reference of 35180-01-9, 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. 35180-01-9 name is Chloromethyl isopropyl carbonate, 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.

Diesterification reaction: Under a nitrogen atmosphere, 100 g Tenofovir (PMPA) And 300ml N-methylpyrrolidone (NMP), the control temperature at 25 ~ 30 , shaking 30min, To dissolve, and then add 106g triethylamine (TEA), 20 ~ 30 shaking 30min until uniform; The above mixture was warmed to 60 ~ 65 , and stirred, In 15 ~ 20min rapid dropping 266g chloromethyl isopropyl carbonate (CMIC) Then warmed to 75 ~ 80 , shaking reaction 60 ~ 70min, When TLC real-time monitoring of the basic reaction of the reaction material completely (3% or less), and monoester content of 15% or less, When the area of the main peak of the product is more than 80%, the double esterification reaction is complete; Then the reaction system first use water bath cooling 5min, After using ice-water bath in 10-15 min the reaction system rapidly reduced to 10-15 ;Extraction and Separation: To the reaction system in step (1) was added 600 ml of ethyl acetate (EA) Heated at 10 ~ 15 , stirred for 15min and filtered, each time with 200ml ethyl acetate (EA) washed the filter cake three times, And the filtrate and the resulting filtrate was combined, to which was added 400ml 10 ~ 15 distilled cold water, Full shock, extraction and separation, the separated aqueous phase was extracted with ethyl acetate twice, The resulting organic phase was combined with the EA layer, washed twice with 1000 ml of distilled water, 300g of sodium chloride was added into the obtained water washing solution twice, dissolved with stirring and cooled down to 10 to 15 C, And then extracted with 500ml of ethyl acetate once, the organic phase was extracted and combined, Washed with 900 to 1000 ml of saturated saline (300 g of sodium chloride dissolved in 850 ml of distilled water) Finally, the organic phase was added 400g anhydrous sodium sulfate 60min after drying filtration;Salt-forming reaction: to step (2) dried and filtered about 2000ml filtrate was added to the reaction vessel, Then 32g fumaric acid (FMA) was added and the temperature was raised to 40 C in a nitrogen atmosphere and the reaction was stirred until the solution became clear. (4) Preparation of tenofovir disoproxil fumarate crude product: Step (3) The reaction solution was concentrated under reduced pressure at 40 C, most of the solvent was distilled off until a large amount of crystals were precipitated, Then the concentrate was naturally cooled to room temperature, and then placed in a -5 C freezer was allowed to cool more than 2h, filtered, The resulting filter cake was washed with a small amount of ethyl acetate 2 to 3 times, pumping dry weighed about 130g, 40 under blast drying 2h, weighed to give 85g Tenofovir disoproxil fumarate crude product, The HPLC detector purity of 98% or more;Recrystallization: Under a nitrogen atmosphere, the reaction vessel was charged with step (4) 85 g crude Tenofovir disoproxil fumarate and 500 ml isopropanol (IPA) The nitrogen atmosphere was warmed to 55 C and stirred for 15 min to clarify the solution. If not, the filtrate should be filtered and the filtrate rapidly crystallized. After the resulting solution was left to cool to room temperature, Placed in a freezer at 4 frozen 2h above, so recrystallized, filtered, rinsed with cold isopropyl alcohol cake, Drained, to obtain white wet crystal 108g, at 40 blast drying 2h or 40 under reduced pressure drying 4h, 72 g of tenofovir disoproxil fumarate finished product was obtained. Tenofovir disoproxil fumarate obtained by the above method was tested by HPLC, Its purity is higher than 99.5%, monoester is less than 0.5%, the sum of other impurities is not more than 0.1%, with tenofovir, The total molar yield is about 35-40%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Chloromethyl isopropyl carbonate, and friends who are interested can also refer to it.

Reference:
Patent; Jiangsu Han Sitong Pharmaceutical Co., Ltd.; Wang Duoping; Wei Genghu; Shi Jiagui; Yang Yu; (7 pag.)CN107400145; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, 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 3618-04-0, Quality Control of trans-Ethyl 4-hydroxycyclohexanecarboxylate

To a solution of ethyl 4-hydroxycyclohexanecarboxylate (5.00 g, 29.0 mmol) in dichloromethane (30 mL) was added 3,4-dihydro-2H-pyran (2.52 g, 29.0 mmol) and Amberlyst 15 (0.5 g). The reaction mixture was stirred at room temperature for 72 h, then another prtion 3,4-dihydro-2H-pyran (1.89 g, 21.8 mmol) and Amberlyst 15 (0.5 g) was added, then after 5 h the reaction mixture was washed with sat. aq. sodium hydrogencarbonate solution. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated to afford the title compound as a yellow oil (9 g), which was used directly in the next step.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; DEHMLOW, Henrietta; MARTIN, Rainer E.; MATTEI, Patrizio; OBST SANDER, Ulrike; RICHTER, Hans; WO2013/60653; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 122-72-5,Some common heterocyclic compound, 122-72-5, name is 3-Phenylpropyl Acetate, molecular formula is C11H14O2, 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.

General procedure: In a typical example, a substituted benzene (1.0mmol), as shown in Table 6, was treated with H2 (30atm) with stirring at 30 or 50C in the presence of Ru-1 (Ru=0.003mmol, S/C=333, in 1mL of H2O) in an autoclave with an inner glass tube. The product was extracted with EtOAc (3mL¡Á5) and the combined extracts were dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified using a short silica gel column. The hydrogenation of anisole on a large scale [toluene=24mmol (S/C=1400)] is described in the Supplementary data.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Phenylpropyl Acetate, its application will become more common.

Reference:
Article; Gao, Lei; Kojima, Keisuke; Nagashima, Hideo; Tetrahedron; vol. 71; 37; (2015); p. 6414 – 6423;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 35598-05-1, These common heterocyclic compound, 35598-05-1, name is Methyl 4-methoxy-2-methylbenzoate, 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.

[00121] Step 1 : Methyl 2-(bromomethyl)-4-methoxybenzoate[00122] To a solution of methyl 4-methoxy-2-methylbenzoate (1 g, 5.6 mmol) inCC14 (25 mL) was added dropwise N-bromosuccinimide (1.1 g, 6.2 mmol) previously dissolved in CC14 (5 mL) and a catalytic amount of benzoyl peroxide. The mixture was refluxed for 2 hours, cooled to room temperature and poured onto iced water. The aqueous mixture was extracted with DCM (3x), and the combined organics were dried over MgS04, filtered, and concentrated in vacuo to provide 2.1 g of the titled product as light yellow solid (~ 100% yield): [M+H+] m/z 260.

Statistics shows that Methyl 4-methoxy-2-methylbenzoate is playing an increasingly important role. we look forward to future research findings about 35598-05-1.

Reference:
Patent; SELEXAGEN THERAPEUTICS, INC.; VERNIER, Jean-Michel; MAY, John; O’CONNOR, Patrick; RIPKA, William; PINKERTON, Anthony; BOUNAUD, Pierre-Yves; HOPKINS, Stephanie; WO2011/85128; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 27829-72-7, name is Ethyl E-hex-2-enoate, molecular formula is C8H14O2, 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. Computed Properties of C8H14O2

(1) Ethyl 2,3-methanohexanoate 15.6 g. of sodium hydride (content 65.1percent, 0.423 mol) were suspended in 800 ml. of dimethyl sulphoxide, and there were added, with stirring, 154 g. (0.7 mol) of trimethyloxosulphonium iodide in small portions at 20¡ã to 30¡ãC. over a period of 20 minutes. An exothermic reaction took place with the evolution of hydrogen. After stirring for 10 minutes, there was added, dropwise, a solution of 60 g. (0.423 mol) of ethyl hex-trans-2-enoate in 70 ml. of dimethyl sulphoxide at 20¡ã to 30¡ãC. The reaction mixture was stirred at 40¡ãC. for 3 hours and then poured into 2 litres of ice-water and extracted with diethyl ether. The aqueous layer was treated with 60 ml. of concentrated hydrochloric acid and extracted with diethyl ether. The combined ethereal layer was washed with water, dried with magnesium sulphate and concentrated under reduced pressure. Distillation of the crude product gave 23.2 g. of ethyl 2,3 -methanohexanoate having the following physical characteristics:- b.p. 57¡ã to 60¡ãC./6 mm.Hg; NMR (CDCl3 and CCl4 solution); delta: 4.05 (2H, q), 0.95 (3H, t) and 0.70-0.48 (2H, dd); IR (liquid film); nu: 2950, 1720, 1450, 1405, 1370, 1330, 1265, 1200, 1180, 1100, 1040, 860 cm-1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 27829-72-7, its application will become more common.

Reference:
Patent; Ono Pharmaceutical Co., Ltd.; US3978229; (1976); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 2435-36-1,Some common heterocyclic compound, 2435-36-1, name is Dimethyl cyclopentane-1,3-dicarboxylate, molecular formula is C9H14O4, 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 solution of HMPA (13.08 mL, 75 mmol) and LDA (13.43 mL, 26.9 mmol) in THF (30 mL) was added a solution of dimethyl cyclopentane-1, 3-dicarboxylate (2 g, 10.74 mmol) in 10 mL THF dropwise over 30 minutes at -78 under N2protection and stirred at one point for another 30 minutes. The solution was warmed to 0 and stirred at one point for 1 hour. The solution was cooled to -78 and added a solution of 1-bromo-2-chloroethane (1.848 g, 12.89 mmol) in 10 mL THF dropwise. The solution was stirred at -78 for 1 hour and warmed to RT. Afrer stirred for 16 hours, the solution was added 1N HCl and extracted with EtOAc. The combined organic layer was dried over Na2SO4, concentrated in vacuo to give the title compound.1H NMR (CDCl3400 MHz) : 3.67 (s, 6H) , 2.01 (d, J6.7 Hz, 4H) , 1.89 (s, 2H) , 1.66 (d, J6.7 Hz, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl cyclopentane-1,3-dicarboxylate, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph A.; ALHASSAN, Abdul-Basit; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; WANG, Jyhshing; YU, Wensheng; CAI, Jiaqiang; LIU, Shilan; WANG, Dahai; WU, Hao; YANG, Chundao; (260 pag.)WO2016/106623; (2016); A1;,
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Ester – an overview | ScienceDirect Topics