Dioxole related

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

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO408,mainly used in chemical industry, its synthesis route is as follows.,144690-92-6

Trityl olmesartan medoxomil (8 g, 10 mmol) is dissolved in THF (50 ml) and 48 % aqueous hydrobromic acid (3.5 ml, 30 mmol) is added. The mixture is stirred for 1 hour at room temperature and then 1 hour at 0 C. The precipitate is filtered, washed with cold THF (20 ml) and dried overnight in vacuum at room temperature to give 5.7 g of olmesartan medoxomil hydrobromide Form B (98.6 % area)

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; LEK Pharmaceuticals d.d.; EP2022790; (2009); 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

The reaction flask was charged with 400 g of compound VII (0.50 mol) and 70% aqueous acetic acid solution of 3200 ml, Reaction was carried out at 50 C for 2 hours. After the completion of the reaction, the solvent was concentrated and concentrated, and ammonia was added to the residue.PH = 7, extracted with 1400 ml of ethyl acetate, the ethyl acetate layer was washed with water, and finally with anhydrous sodium sulfateDried; filtered, the filtrate was concentrated to dryness and the residue was recrystallized from ethanol to give the compound I pure product 256.1G, yield: 91.79%.

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; Hunan Ouya biological Co. Ltd.; Lin, kaizhao; (19 pag.)CN103304550; (2016); B;,
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: C8H14ClNO254,mainly used in chemical industry, its synthesis route is as follows.,80841-78-7

Example 1(1) Tritylation and DMDO Esterification ReactionsAfter mixing 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[[2′-[1H-tetrazol-5-yl]biphenyl-4-yl]methyl]imidazole-5-carboxylic acid (30 g), acetone (210 mL), 1,8-diazabicyclo[5,4,0]-7-undecene [DBU] (25.5 g) and triphenylmethyl chloride [TPC] (23.79 g), water (0.6 mL) was added and acetone (30 mL) was poured into the mixture, and the reaction mixture was stirred at 48 to 52 C. for 2 hours. Then, water (0.9 mL) was added and 4-chloromethyl-5-methyl-1,3-dioxol-2-one [DMDO-Cl] (18.5 g) was poured in, and the reaction mixture was stirred at 48 to 52 C. for 5 hours.(2) Obtaining Crude Crystals of Trityl Olmesartan Medoxomil (Acetone Solvate Crystals)After the reaction mixture was cooled to 20 C. to precipitate crystals, it was stirred at 15 to 25 C. for 40 minutes, and water (96 mL) was added dropwise over a period of 25 minutes, and then the reaction mixture was cooled to 0 to 5 C. and stirred for 30 minutes. The precipitated crystals were filtered out and washed with acetone-water (150 mL), and wet crude crystals of (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[[2′-[2-(triphenylmethyl)-2H-tetrazol-5-yl]biphenyl-4-yl]methyl]imidazole-5-carboxylate (57.83 g) were obtained. These were then dried in vacuo at 60 C. for approximately 15 hours, and the dry acetone solvate crystals (57.50 g) were 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; DAIICHI SANKYO COMPANY, LIMITED; US2012/59172; (2012); A1;,
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

Step B, go to the reaction solution of compound (II) obtained in Step A with stirring,Add 6.27kg of anhydrous potassium carbonate powder and2.01kg iodine, replace the air with nitrogen, the nitrogen pressure in the kettle is ?0.01Mpa,The temperature was controlled at 50 ¡À 2 , and 13.80 kg of compound (IV) was added dropwise at a constant pressure.Add within 40 to 60 minutes. After the incubation reaction for 1.25 hours,Reduce the reaction mixture to below 10 C, extract with conventional solvents in an extraction kettle, wash with water, and separate the layers.The organic phase was distilled under reduced pressure to recover the solvent, crystallized, centrifuged,Drying gave 55.03 kg of crude compound (I).Step C: Add 192.61 kg of ethyl acetate to the 500L refining kettle, start stirring,55.03 kg of the crude compound (I) obtained in step B is added, and the feeding port is closed,Keep the pressure ?0.01MPa after replacing air with nitrogen,The temperature was raised to 75 C and dissolved for 25 minutes until it was clear. The filtrate was filtered and the temperature was reduced to 2.5 C.Centrifuge, put the filter cake into the double cone dryer,Under reduced pressure, a small flow of nitrogen was passed in for replacement three times, and the drying temperature was controlled to 40-50 C.Vacuum degree ?-0.09MPa, after drying for 1 hour,Increase the drying temperature to 50 60 and continue drying for 3 hours.54.06kg compound (1) finished product,The HPLC content was 99.93%, and the residual content of the compound (III) was 0.05%.

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; Shandong Xinhua Pharmaceutical Co., Ltd.; Zhu Lianbo; Wu Hui; Dou Guohua; (6 pag.)CN110590758; (2019); A;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem