Dioxole related

4-(Chloromethyl)-5-methyl-1,3-dioxol-2-one, A common heterocyclic compound, 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.”80841-78-7

Example 1; Preparation of olmesartan medoxomilTo dimethyl acetamide (300 ml) was added 4-(1-hydroxy-1-methylethyl)-2-propyl imidazol- 5-carboxylic acid ethyl ester (50 gms) and powdered sodium hydroxide (26 gms). To this, 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide (135 gms) was charged at 45-500C. The contents were stirred for 5 hours at 45-500C. Diisopropylethyl amine (100 ml) was charged to the reaction mass at 40-450C. A solution of 5-methyl-2-oxo-1 , 3-dioxane-4-yl)methyl chloride (80 gms) diluted with dimethyl acetamide (160 ml) was slowly added to the reaction mass at 40-450C over a period of 1 hour. The contents were heated to 60-650C and maintained for 4 hours. The reaction mass was then cooled to 30-350C and neutralized with concentrated hydrochloride acid. The reaction mass was filtered to remove inorganic impurities, charcoalized using charcoal (10 gms) andstirred for 30 minutes at 40-450C. The reaction mass was filtered over hyflo. The clear filtrate was acidified with hydrochloric acid (100 ml) slowly at 25-30C. The contents were stirred at 60C for 1 hour. The reaction mass was chilled to 0-5C and filtered to remove tritanol. The reaction mass was concentrated under reduced pressure. The residue was quenched with water (500ml), neutralized with base and extracted in dichloromethane (500 ml). The clear dichloromethane extract was then concentrated under reduced pressure and stripped off with acetone. The residue thus obtained was isolated from acetone (250 ml) to give 55 gms of the title compound. Chromatographic purity- > 99%; Example 2Preparation of olmesartan medoxomilTo dimethyl acetamide (600 ml) was added 4-(1-hydroxy-1-methylethyl)-2-propyl imidazol- 5-carboxylic acid ethyl ester (100 gms) and powdered potassium hydroxide (50 gms). To this was charged 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide (270 gms) at 45-50C. The contents were stirred for 5 hours at 45-50C. Diisopropylethyl amine (200 ml) was charged to the reaction mass at 40-450C. To this was slowly added a solution of 5-methyl-2-oxo- 1 ,3-dioxane-4-yl)methyl chloride (160 gms) diluted with dimethyl acetamide (320 ml) at 40- 45C over a period of 1 hour. The contents were heated to 60-650C and maintained for 4 hours. The reaction mass was then cooled to 30-350C and was neutralized with concentrated hydrochloride acid. The reaction mass was filtered to remove inorganic impurities. The reaction mass was charcoalized using charcoal (20 gms) and was stirred for 30 minutes at 40-450C. The reaction mass was filtered over hyflo. The clear filtrate was acidified with hydrochloric acid (200 ml) slowly at 25-300C. The contents were stirred at 60C for 1 hour. The reaction mass was chilled to 0-50C and was filtered to remove tritanol. The reaction mass was concentrated under reduced pressure. The residue was quenched with water (1000 ml), neutralized with base and extracted in dichloromethane (1000 ml). The clear dichloromethane extract was then concentrated under reduced pressure, stripped off with acetone. The residue thus obtained was isolated from the acetone (500 ml) to give 110 gms of the title compound. Chromatogrphic purity- > 99%; Example 4Preparation of trityl olmesartan medoxomilTo dimethyl acetamide (300 ml) was added 4-(1-hydroxy-1-methylethyl)-2-propyl imidazol- 5-carboxylic acid ethyl ester (50 gms) and powdered potassium hydroxide (25 gms). To this was charged 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide (135 gms) at 45-500C. The contents were stirred for 5 hours at 45-500C. Diisopropylethyl amine (100 ml) was charged to the reaction mass at 40-45C. To this was slowly added a solution of 5-methyl-2-oxo- 1 ,3-dioxane-4-yl) methyl chloride (80 gms) diluted with dimethyl acetamide (160 ml) at 40- 45C over a period of 1 hour. The contents were heated to 60-650C and maintained for 4 hours. The reaction mass was then cooled to 30-350C. and was neutralized with concentrated hydrochloride acid. The reaction mass was filtered to remove inorganics. The reaction mass was charcoalized using charcoal (10 gms) and was stirred for 30 minutes at 40-450C. The reaction mass was filtered over hyflo. The clear filtrate was quenched with purified water(200 ml)at 25-30C over a period of 3-4 hours. The contents were stirred at 25-300C for 30 minutes. Crude trityl olmesartan medoxomil was isolated by filtration, slurried in water (500 ml), centrifuged and dried under reduced pressure at 45-50C.

The chemical industry reduces the impact on the environment during synthesis, 4-(Chloromethyl)-5-methyl-1,3-dioxol-2-one, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; CIPLA LIMITED; CURTIS, Philip, Anthony; WO2008/43996; (2008); A2;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

144690-92-6, A common heterocyclic compound, 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.”144690-92-6

Trityl olmesartan medoxomil (250 g, 310 mmol) (97.3 % area) is dissolved in THF (1560 ml) and 48 % aqueous hydrobromic acid (70.6 ml, 625 mmol) is added slowly. The mixture is stirred for at 25 C. After 1 hour the precipitate forms. The mixture is stirred for 1 additional hour at 25 C, then cooled to -5 C and stirred for 1.5 hours at -5 C. The precipitate is filtered. 940 ml of THF is added to the precipitate and the mixture is stirred for 1 h at 25 C and then 1 hour at -5 C. Then precipitate is filtered off and washed with cold THF (150 ml). It is then dissolved in a mixture of water (875 ml) and acetone (440 ml). To a clear solution 5 % aqueous solution of NaHCO3 is added to raise pH to 5.15. The mixture is stirred for 1 hour at room temperature and 1 hour at 0 C. The precipitate is filtered, washed with water and then recrystallized from a mixture of acetonitrile (280 ml) and water (70 ml) to give 124.5 g of olmesartan medoxomil (99.68 % area)

With the complex challenges of chemical substances, we look forward to future research findings about Triphenyl methyl olmesartan

Reference£º
Patent; LEK Pharmaceuticals d.d.; EP2022790; (2009); A1;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

4-(Chloromethyl)-5-methyl-1,3-dioxol-2-one, A common heterocyclic compound, 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.”80841-78-7

Example 4; The reaction was carried out in the same manner as in Example 1 except that 4- (1-hydroxy-1-methylethyl) -2-propyl-1- {4- [2- (trityltetrazol-5-yl) phenyl] -carboxylic acid sodium salt (Chemical Formula 5) and 50 mL of N, N-dimethylacetamide were added, the temperature was adjusted to 5 to 10 DEG C and 4 g of potassium carbonate was added. A solution of 6.2 g of 4- (chloromethyl) -5-methyl-1,3-dioxol-2-one (Formula 6) in 6 mL of N, N-dimethylacetamide was added dropwise to the reaction portion, For 4 hours. After the reaction was completed, the reaction solution was cooled to 20 to 25 C, and then 220 mL of ethyl acetate, 30 g of salt, and 170 mL of purified water were sequentially added to the reaction mixture, followed by separation of the organic layer, followed by the addition of 30 g of salt and 170 mL of purified water . & Lt; / RTI & gt; 1 g of activated carbon and 20 g of anhydrous sodium sulfate were added to the organic layer, followed by stirring for 30 minutes to 1 hour, followed by filtration. The filtrate was concentrated under reduced pressure, and 100 mL of acetonitrile was added to the residue, followed by stirring at 50 to 55 DEG C for 1 hour. The crystals were cooled to 0 to 5 C., stirred for 2 hours, filtered, washed with 50 mL of isopropyl alcohol and dried to obtain 21.7 g (yield: 93%, purity: 99.96%) of tritylolemethanemethoxysilane

The chemical industry reduces the impact on the environment during synthesis, 4-(Chloromethyl)-5-methyl-1,3-dioxol-2-one, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; DONGBANG FTL CO., LTD; Song, Tae Hong; Jung, Hun Suk; Jang, Do Yeon; Moon, Chung Sun; Jung, Hee Jung; (18 pag.)KR101526249; (2015); B1;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

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.37830-90-3, 4,5-Dimethyl-1,3-dioxol-2-one it is a common compound, a new synthetic route is introduced below.37830-90-3

5. 0kg adding the compound of formula (IV) in a reaction vessel, 8. 0kg N- bromosuccinimide (NBS), 0. 30kg of azobisisobutyronitrile was added as the reaction solvent chloroform 100L, stirring was warmed to 38 ¡ã C, the reaction system to be stable, then slowly heated to reflux for 2-3 hours, the reaction was completed, cooled to room temperature, insolubles were removed by filtration, the filtrate was atmospheric recovery chloroform, 4 ¡ã C refrigerated overnight and filtered again after crystallization the insoluble matter was removed, and then distilled under reduced pressure collecting ll ¡ã C~120 ¡ã C / 5mmHg fractions, the compound of formula (V) 8. 66kg, yield (mole) 938percent, purity 95.1percent.;

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 4,5-Dimethyl-1,3-dioxol-2-one reaction routes.

Reference£º
Patent; Jumpcan Pharmaceutical Group/ji chuan(jiang su)Jumpcan Pharmaceutical Group co.ltd; cao, Longxiang; dong, Zibo; niu, ben; shao, Jianguo; (12 pag.)CN103113392; (2016); B;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

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.37830-90-3, 4,5-Dimethyl-1,3-dioxol-2-one it is a common compound, a new synthetic route is introduced below.37830-90-3

[01658] A solution of 4,5-dimethyl-2-oxo-1,3-dioxolene (1 mmole) and selenium dioxide (2.5 mmole) in dioxane was heated at reflux for 1 h. Evaporation, extraction and chromatography gave 5-methyl-4-hydroxymethyl-2-oxo-1,3-dioxolene as a yellow oil. TLC: RPf=0.5, 5percent MeOH-dichloromethane. [01659] A solution of 5-methyl-4-hydroxymethyl-2-oxo-1,3-dioxolene (1 mmole) in DMF was treated with tert-butyldimethylsilane (1.2 mmole) and imidazole (2.2 mmole) at 25 C. for 24 h. Extraction and chromatography gave 5-methyl-4-tert-butyldimethylsilyloxymethyl-2-oxo-1,3-dioxolene. [01660] A solution of 5-methyl-4-tert-butyldimethylsilyloxymethyl-2-oxo-1,3-dioxolene (1 mmole) and Lawesson’s reagent (1.2 mmole) in toluene was heated to 120 C. for 12 h. Extraction and chromatography gave 5-methyl-4-tert-butyldimethylsilyloxymethyl-2-thio-1,3-dioxolene. [01661] A solution of 5-methyl-4-tert-butyldimethylsilyloxymethyl-2-thio-1,3-dioxolene in methanolic hydrogen chloride was stirred at 0 C. for 1 h and 25 C. for 12 h. Extraction and chromatography gave 5-methyl-4-hydroxymethyl-2-thio-1,3-dioxolene.

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 4,5-Dimethyl-1,3-dioxol-2-one reaction routes.

Reference£º
Patent; Metabasis Therapeutics, Inc.; US6756360; (2004); B1;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

144690-92-6, A common heterocyclic compound, 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.”144690-92-6

A solution of MTT in an organic solvent and water (20%) was heated for 4-8 hrs at reflux. When the solvents were either acetonitrile (ACN), isopropyl alcohol (IPA) or t-butanol (t-BuOH), 1 volume of water was added, and the reaction was stirred until the amount of MTT was less than 2%. The mixture was evaporated to dryness. Ethyl acetate (EtOAc, 1 volume) was added to the residue and then evaporated again (twice). The resulting solid was dissolved in EtOAc (12 vol) and heated to reflux. The solution was cooled (2 C.) and stirred for 2 hrs. The product was filtered, washed (EtOAc, 1 vol), and dried on vacuum (45 C.). Table 1 shows the process details with different organic solvents: TABLE 1 Total solvent Time Solvent(s) Volume Temperature ( C.) (hrs) pH ACN:H2O 5:1 + 1 85 7 4.89-4.3 IPA:H2O 5:1 + 1 85 7 4.62-4.25t-BuOH:H2O 5:1 + 1 85 7 4.78-4.28n-propanol:H2O 5:1 reflux 2.5 4.3n-BuOH:H2O 5:1 110 2.5 4.412-BuOH:H2O 5:1 100 3 4.5iso-penthanol:H2O 5:1 100 3 5DMA:H2O 5:1 100 4 4.5DMF:H2O 5:1 100 4 4.5, 144690-92-6

As the rapid development of chemical substances, we look forward to future research findings about 144690-92-6

Reference£º
Patent; Hedvati, Lilach; Pilarsky, Gideon; Shenkar-Garcia, Natalia; US2006/148870; (2006); A1;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

Triphenyl methyl olmesartan, A common heterocyclic compound, 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.”144690-92-6

A mixture of trityl olmesartan medoxomil in acetic acid and water (1:1, 400 mL) and sulfuric acid (12.2 gm) (1 mol equivalent) was stirred at 25C-30C for 45-60 minutes. Triphenylcarbinol was filtered and the filtrate was washed with acetic acid and water mixture (1:1, 50 rnL). Sodium carbonate solution (25% w/v, 100 mL) was charged to the filtrate and the product was extracted with dichloromethane (500 mL) followed by recovery of the solvent. The product was isolated, recrystallized using acetonitrile (300 mL), filtered, washed and dried under reduced pressure to obtain crude olmesartan medoxomil.Yield: 90% HPLC purity: 99.29 % OLM-acid: Not Detectable OLM- Eliminate: 0.07% Acetic acid content: Not Detectable

The chemical industry reduces the impact on the environment during synthesis, Triphenyl methyl olmesartan, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; RANBAXY LABORATORIES LIMITED; KAPOOR, Ashwini, Kumar; MEHTA, Hiten, Sharadchandra; NATH, Asok; PRASAD, Mohan; WO2010/134052; (2010); A1;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

144690-92-6, A common heterocyclic compound, 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.”144690-92-6

To 3L reaction flask 165.3g above prepared 1 – [[[2- (triphenylmethyl) -2H- tetrazole-5-yl] biphenyl-4-yl] methyl] -2- propyl-4- (1-hydroxy-1-methylethyl) imidazole-5-carboxylic acid (5-methyl-2-oxo-1,3-dioxolen-4-yl) methyl ester ( compound ) and 1.90L70% acetic acid, mechanical stirring, heated to 50 , the reaction 2.5h, an ice bath was added 1.1L of water was stirred.Filtration, the filtrate with 300ml * 3 times extracted with methylene chloride, the methylene chloride phase 150mL ¡Á 5 times with 5% acetic acid solution was washed with acetic acid solution and extracted with 250ml of dichloromethane, and the combined organic phases.The solvent was distilled off under reduced pressure, the residue was added 380mL of ethyl acetate was heated with stirring and cooling to precipitate a solid.Suction filtered, the filter cake was dried in vacuo to give a white solid product to 89.6 g, weight yield was 77.8%.To a 1L reaction flask above 85g crude product olmesartan medoxomil, 420ml of tetrahydrofuran was heated at reflux, was added 360ml of ethyl acetate, the ice bath was stirred for crystallization.Filtration cake blast drying to constant weight to give the product as a white solid 74.8g, a yield of 83.5% by weight., 144690-92-6

As the rapid development of chemical substances, we look forward to future research findings about 144690-92-6

Reference£º
Patent; Bengbu Tu Shan Fengyuan Pharmaceutical Co., Ltd.; Ma, Qisheng; Li, Baoqin; Sun, Peng; (18 pag.)CN105418593; (2016); A;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

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.144690-92-6, Triphenyl methyl olmesartan it is a common compound, a new synthetic route is introduced below.144690-92-6

A solution of MTT in an organic solvent and water (20%) was heated for 4-8 hrs at reflux. When the solvents were either acetonitrile (ACN), isopropyl alcohol (IPA) or t-butanol (t-BuOH), 1 volume of water was added, and the reaction was stirred until the amount of MTT was less than 2%. The mixture was evaporated to dryness. Ethyl acetate (EtOAc, 1 volume) was added to the residue and then evaporated again (twice). The resulting solid was dissolved in EtOAc (12 vol) and heated to reflux. The solution was cooled (2 C.) and stirred for 2 hrs. The product was filtered, washed (EtOAc, 1 vol), and dried on vacuum (45 C.). Table 1 shows the process details with different organic solvents: TABLE 1 Total solvent Time Solvent(s) Volume Temperature ( C.) (hrs) pH ACN:H2O 5:1 + 1 85 7 4.89-4.3 IPA:H2O 5:1 + 1 85 7 4.62-4.25t-BuOH:H2O 5:1 + 1 85 7 4.78-4.28n-propanol:H2O 5:1 reflux 2.5 4.3n-BuOH:H2O 5:1 110 2.5 4.412-BuOH:H2O 5:1 100 3 4.5iso-penthanol:H2O 5:1 100 3 5DMA:H2O 5:1 100 4 4.5DMF:H2O 5:1 100 4 4.5

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 Triphenyl methyl olmesartan reaction routes.

Reference£º
Patent; Hedvati, Lilach; Pilarsky, Gideon; Shenkar-Garcia, Natalia; US2006/148870; (2006); A1;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

Triphenyl methyl olmesartan, A common heterocyclic compound, 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.”144690-92-6

78(b) (5-Methyl-2-oxo-1,3-dioxolen-4-yl)methyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(tetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate 75 ml of water were added to a suspension of 29.3 g of (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate [prepared as described in step (a) above] in 225 ml of acetic acid, and the resulting mixture was stirred at 60 C. for 1.5 hours. At the end of this time, 75 ml of water were added to the mixture, which was then cooled. Precipitated trityl alcohol was removed by filtration, and the filtrate was concentrated by evaporation under reduced pressure. Toluene was added to the residue, and the mixture was again concentrated by evaporation under reduced pressure, to remove the remaining water and acetic acid. The residue was crystallized in ethyl acetate, to give 16.6 g of the title compound as crystals, melting at 177-180 C. (with decomposition). The Nuclear Magnetic Resonance Spectrum of this compound was identical with that of the compound obtained as described in Example 61(b).

The chemical industry reduces the impact on the environment during synthesis, Triphenyl methyl olmesartan, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Sankyo Company, Limited; US5616599; (1997); A;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem