Month: September 2020

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO399,mainly used in chemical industry, its synthesis route is as follows.,37830-90-3

Example 17 Preparation of 5-methyl-4-hydroxymethyl-2-oxo-1,3-dioxolene A solution of 4,5-dimethyl-2-oxo-1,3-dioxolene (1 mmol) and selenium dioxide (2.5 mmol) 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: Rf=0.5, 5percent MeOH-dichloromethane.

With the synthetic route has been constantly updated, we look forward to future research findings about 4,5-Dimethyl-1,3-dioxol-2-one,belong Dioxole compound

Reference£º
Patent; Metabasis Therapeutics, Inc.; US6284748; (2001); B1;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO409,mainly used in chemical industry, its synthesis route is as follows.,80841-78-7

Example 3; Preparation of olmesartan medoxomilTo dimethyl acetamide (800 ml) was added 4-(1-hydroxy-1-methylethyl)-2-propyl imidazol- 5-carboxylic acid ethyl ester (100 gms) and powdered potassium carbonate (200 gms). To this was charged 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide (300 gms) at 45-50C. The contents were stirred for 8-10 hours at 45-50C. The insolubles were filtered. The contents were cooled to 5-100C. Potassium tertiary butoxide (100 gms) was charged at a temperature below 45C. The reaction was maintained at 40-450C for 3 hrs. To this was slowly added 5-methyl-2-oxo-1 ,3-dioxane-4-yl) methyl chloride 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 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 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 was filtered to remove tritanol. The reaction mass was concentrated under reduced pressure. The residue was quenched with water (500 ml), neutralized with base and extracted in dichloromethane (500 ml).The clear dichloromethane extract was then concentrated under reduced pressure, stripped off with acetone. The residue thus obtained was isolated from the acetone (250 ml) to give 55 gms of the title compound. Chromatogrphic purity- > 99%

With the synthetic route has been constantly updated, we look forward to future research findings about 4-(Chloromethyl)-5-methyl-1,3-dioxol-2-one,belong Dioxole compound

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

As a common heterocyclic compound, it belong Dioxole compound,4,5-Dimethyl-1,3-dioxol-2-one,37830-90-3,Molecular formula: C5H6O3,mainly used in chemical industry, its synthesis route is as follows.,37830-90-3

(1) 4-Bromomethyl-5-methyl-1,3-dioxolen-2-one [compound of formula (III) in which R is methyl and X is bromine] 3.42 g of 4,5-dimethyl-1,3-dioxolen-2-one [compound of formula (III’) in which R is methyl, prepared in accordance with the procedure described in Tetrahedron Letters, pages 1701-1704, (1972)] was dissolved in 150 ml of carbon tetrachloride. To the solution were added 5.34 g of N-bromosuccinimide and a catalytic amount of alpha,alpha’-azobisisobutyronitrile. The mixture was heated under reflux for 15 minutes. The reaction mixture was cooled with ice, and the insoluble materials were removed by filtration. The filtrate was concentrated under reduced pressure to give a syrupy residue. The residue was distilled under reduced pressure, and a fraction having a boiling point of 115¡ã to 120¡ã C./5 mmHg was recovered. Thus, 4.2 g (yield 73percent) of the captioned compound having the following properties was obtained as a colorless liquid. Elemental analysis for C5 H5 BrO3: IR (neat) nu(cm-1): near 18 25 (carbonyl). NMR (CCl4) delta(ppm): 2.10 (3H, –CH3, s), 4.10 (2H, –CH2 Br, s).

With the synthetic route has been constantly updated, we look forward to future research findings about 4,5-Dimethyl-1,3-dioxol-2-one,belong Dioxole compound

Reference£º
Patent; Kanebo Ltd.; US4448769; (1984); A;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.144690-92-6,Triphenyl methyl olmesartan,as a common compound, the synthetic route is as follows.,144690-92-6

Example 2 Olmesartan medoxomil of formula I20 g of the starting compound of formula III were stirred up in 75 ml of acetic acid and after stirring for 10 minutes 30 ml of water were added dropwise during 5 minutes. Then, the suspension was put in a 50C bath and stirred for 4 hours. Then 16 ml of water were added dropwise in 5 minutes, the mixture was taken out of the bath and after 5 minutes it was put in a cooling bath with the temperature of 10C. After 20 minutes the separated insoluble fraction, containing the side product trityl alcohol, was aspirated and washed with a mixture of 4 ml of AcOH + 2 ml of water. 40 ml of acetone and then 70 ml of water were added to the filtrate at 30C, the separated product was aspirated and 1 1.5 g (82 %) of the product were obtained.

As the paragraph descriping shows that 144690-92-6 is playing an increasingly important role.

Reference£º
Patent; ZENTIVA, K. S.; STACH, Jan; JARRAH, Kamal; KRULIS, Radim; RADL, Stanislav; CERNY, Josef; WO2012/55380; (2012); A1;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

As a common heterocyclic compound, it belong Dioxole compound,Triphenyl methyl olmesartan,144690-92-6,Molecular formula: C48H44N6O6,mainly used in chemical industry, its synthesis route is as follows.,144690-92-6

A 250 round bottom flask was loaded with MTT (10 g), acetone/water (2/2 vol.), and 3 eq of H2SO4. The mixture was stirred at 40 C., and after 2-4 hrs, triphenyl carbinol (TPC) was precipitated by the addition of water and filtrated out. NaHCO3 was added to the filtrate and the mixture was cooled to room temperature and stirred for 1 hr. Crude olmesartan medoxomil was obtained as white crystals (90% yield).

With the synthetic route has been constantly updated, we look forward to future research findings about Triphenyl methyl olmesartan,belong Dioxole compound

Reference£º
Patent; Hedvati, Lilach; Pilarsky, Gideon; US2006/149078; (2006); A1;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

As a common heterocyclic compound, it belong Dioxole compound,4,5-Dimethyl-1,3-dioxol-2-one,37830-90-3,Molecular formula: C5H6O3,mainly used in chemical industry, its synthesis route is as follows.,37830-90-3

EXAMPLE 1 Preparation of 4-chloro-4-methyl-5-methylene-1,3-dioxolane-2-one (III) To a solution of 50 g of 4,5-dimethyl-1,3-dioxolene-2-one (IV)(Synthesised by the method described in Tetrahedron Letters, 1701-1704 (1972)) in 350 ml of methylene chloride was added 65 g of sulfuryl chloride dropwise over 1 hour at 40¡ã-42¡ã C. The mixture was stirred for one hour at the same temperature and then evaporated in vacuo to remove the solvent. The resulting residue was distilled in vacuo to obtain 42.1 g (65percent of theory) of 4-chloro-4-methyl-5-methylene-1,3-dioxolane-2-one (III) as a colorless oil. B.p. 45¡ã-48¡ã C./2 mmHg. IR(CHCl3)nu(cm-1): 1820, near 1695 etc. NMR(CDCl3, delta(ppm)): 2.19(3H, s, CH3), STR5

With the synthetic route has been constantly updated, we look forward to future research findings about 4,5-Dimethyl-1,3-dioxol-2-one,belong Dioxole compound

Reference£º
Patent; Kanebo, Ltd.; US4554358; (1985); A;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

As a common heterocyclic compound, it belong Dioxole compound,4-(Chloromethyl)-5-methyl-1,3-dioxol-2-one,80841-78-7,Molecular formula: C5H5ClO3,mainly used in chemical industry, its synthesis route is as follows.,80841-78-7

A solution containing about 46 g of compound 4 was taken, 3.5g sodium iodide was added, 280 mL N, N-dimethylformamide, 11.2g DMDO-Cl was slowly added dropwise, 30 Minute addition is completed. After dropping, Heated to 55 , Reaction for 7 hours, The reaction is completely over. filter, Remove insolubles, The filtrate was poured into 700mL of water, Extraction with ethyl acetate, The ethyl acetate layer was collected, dry, filter, The filtrate is concentrated. To the oily substance obtained after the concentration was added 200 mL of ethanol, Stirring, A white solid precipitation, Collect the solid, Washed with 50mL cyclohexane beating, 45.0 g of product was obtained, Two-step total yield of 80.6% The purity of the product was 98% by HPLC.

With the synthetic route has been constantly updated, we look forward to future research findings about 4-(Chloromethyl)-5-methyl-1,3-dioxol-2-one,belong Dioxole compound

Reference£º
Patent; Disha Pharmaceutical Group Co., Ltd.; Zhang Zhaoxing; Zhang Hongqiang; Qin Litai; Li Wei; Li Zongwen; Xia Haijian; (6 pag.)CN103012382; (2016); B;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

Triphenyl methyl olmesartan, cas is 144690-92-6, it is a common heterocyclic compound, the Dioxole compound, its synthesis route is as follows.,144690-92-6

Example 7:Preparation of olmesartan medoxomil Trityl olmesartan medoxomil (260 gm) as obtained in example 1 was dissolved in toluene (2600 ml) and then added concentrated hydrochloric acid (156 ml) for 1 hour 30 minutes at room temperature. The reaction mass was maintained for 1 hour 30 minutes at room temperature and then added water (1000 ml). The reaction mass was stirred for 45 minutes at room temperature and the layers were separated. To the aqueous layer was added ethyl acetate (5000 ml) at room temperature. The reaction mass was cooled to 15 to 20C and pH of the reaction mass was adjusted to 4.5 to 5.5 with sodium carbonate (20%, 560 ml). The reaction mass was stirred for 20 minutes at 20C and the layers were separated. The organic layer was dried over sodium sulfate and ethyl acetate was distilled off completely under vacuum at below 45C to obtain a residual mass. To the residual mass was added ethyl acetate (400 ml) at 40C and then heated to 75 to 80C. The contents were maintained for 30 minutes at 75 to 80C. The reaction mass was cooled to room temperature and stirred for 1 hour. The reaction mass was further cooled to 10 to 15C and stirred for 1 hour 30 minutes, filtered. The solid obtained was dried at 40 to 45C for 4 hours to obtain 150 gm of olmesartan medoxomil.Olmesartan medoxomil: 98.6%;Olmesartan acid impurity: 0.32%;Trityl olmesartan medoxomil impurity: 0.35%Methyl olmesartan medoxomil impurity: 0.35%.

With the synthetic route has been constantly updated, we look forward to future research findings about Triphenyl methyl olmesartan,belong Dioxole compound

Reference£º
Patent; HETERO RESEARCH FOUNDATION; PARTHASARADHI REDDY, Bandi; RATHNAKAR REDDY, Kura; MURALIDHARA REDDY, Dasari; RAJI REDDY, Rapolu; RAMAKRISHNA REDDY, Matta; VAMSI KRISHNA, Bandi; WO2012/1694; (2012); A1;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO36,mainly used in chemical industry, its synthesis route is as follows.,80841-78-7

130 ml of N,N-dimethylacetamide, 14.0 g (20 mmol) of ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl)methyl)-1H-imidazole-5-carboxylate and 2.2 g (16 mmol) of KOH were charged into reaction vessel at room temperature under inert atmosphere. The mixture was stirred at room temperature for 2 h, and then the sample of reaction mixture was analysed (HPLC; starting material 0.2 %, hydrolysed starting material 98.11 %). Then 3.0 g (2.2 mmol) of potassium carbonate powder and 1.4 g (8.4 mmol) of potassium iodide were added. The reaction mixture was cooled to 0 C and 5.0 g (33 mmol) of 4-(chloromethyl)-5-methyl-1,3-dioxol-2-one was added at 0 to 5C. After the addition, the reaction mixture was warmed to 40-45 C within one hour, then the mixture was stirred at this temperature for 2h. The sample of reaction mixture was analysed (HPLC; tritylolmesartan medoxomil 97.22 %, 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl)methyl)-1H-imidazole-5-carboxylate 0.09 %). The mixture was cooled to 10 to 20 C and then 250 ml of ethyl acetate was added. The mixture was cooled again to 5-10 C and then 200 ml of 10 % NaCl was added slowly. The temperature should not be higher than 25 C during the addition. The phases were mixed separated and organic phase was washed with 100 ml of 10 % NaCl (2*) and dried over anhydrous sodium sulphate. After the filtration filtrate was evaporated under reduced pressure at temperature under 45C to oily residue. To the residue 30 ml of acetonitrile was added at temperature not more than 45C. The mixture was stirred at this temperature for 10 minutes then was cooled to 20 to 25C and stirred at this temperature for 0.5 h and after that 3h at 0 to 5C. The suspension was filtered, the cake washed with cold acetonitrile and dried at 40 to 50C. Yield: 17.0 g (94%) HPLC: 99.72 % of the product, all impurities are under 0.1%. IR: 3408, 1818, 1805, 1741, 1681, 1529, 1147, 1003, 699 XRD:

With the synthetic route has been constantly updated, we look forward to future research findings about 4-(Chloromethyl)-5-methyl-1,3-dioxol-2-one,belong Dioxole compound

Reference£º
Patent; Krka Tovarna Zdravil, D.D., Novo Mesto; EP2334668; (2011); A1;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO42,mainly used in chemical industry, its synthesis route is as follows.,80841-78-7

Example 3; Trityl olmesartan medoxomil (III); A solution of potassium salt 4 in methyl ethyl ketone from the preceding experiment (ca. 20 g of the salt) was diluted with methyl ethyl ketone (290 ml), and, after adding potassium iodide (2 g) and 4-chloromethyl-5-methyl-l,3-dioxol-2-one (7 g), the mixture was stirred at 50 0C for 7.5 h. After the reaction was completed, the mixture was filtered, and the filtrate was washed with methyl ethyl ketone (3 x 50 ml). After concentrating to ca. 160 ml in vacuo, ethanol (250 ml) was added, and the reaction mixture was again concentrated to ca. 300 ml in vacuo.The concentrated product in ethanol was inoculated and stirred at 50 0C for 0.5 h, and after getting thicker, diluted with ethanol (50 ml) and cooled to 20 C. The precipitated product was sucked off, washed with ethanol (2 x 20 ml) and dried in a vacuum drier at 50 C. 14.4 g (86 %) of the product was obtained.

With the synthetic route has been constantly updated, we look forward to future research findings about 4-(Chloromethyl)-5-methyl-1,3-dioxol-2-one,belong Dioxole compound

Reference£º
Patent; ZENTIVA, A.S.; WO2007/48361; (2007); A1;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem