Category: 185815-59-2

185815-59-2, 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 3 – SYNTHESIS OF METHYL 3-ISOBUTYL-GLUTARATE (III) A 1 L three-necked round-bottom flask, under nitrogen atmosphere, is loaded with 3-isobutylglutaric anhydride (50.0 g; 0.290 mol) of formula (II), methanol (500 ml) and triethylamine (29.3 g; 0.290 mol); the resulting solution is kept under stirring at room temperature for about 16-18 h. After completion of the reaction, the solvent is evaporated off, the mixture is taken up with water (200 ml), acidified to pH 3-4 with 37% hydrochloric acid and extracted with toluene (3×150 ml). The combined organic phases are evaporated under reduced pressure, to obtain a pale yellow oil (58.6 g; yield: 95%). 1H-NMR (300 MHz, CDCl3, 28C): delta 3.65 (s, 3H); 2.40 (m, 5H); 1.60 (m, 1H); 1.20 (m, 2H); 0.90 (d, 6H)., 185815-59-2

The synthetic route of 185815-59-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Dipharma Francis S.r.l.; EP1992609; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.185815-59-2,4-Isobutyldihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

EXAMPLE 2 Synthesis of 3-(isopropoxycarbonylamino-methyl)-5-methyl-hexanoic acid (IV; R1=isopropyl)A 100 ml three-necked round-bottom flask, under nitrogen atmosphere, is added with 98% hydrazine hydrate (19.5 g, 0.382 mols), sodium hydroxide (12.4 g, 0.309 mol) in water (150 ml) and the solution is cooled to a temperature of -5 C. 3-Isobutyl-glutaric anhydride (183.0 g, 1.075 mol) is dropped therein in about 1-2 h, keeping the temperature below 0-5 C. and the mixture is reacted for about 1 h. 35-37% Hydrochloric acid (450 ml) and toluene (400 ml) are added. Keeping a temperature of -5 C., a solution of sodium nitrite (160.0 g, 2.026 mol) in water (320 ml) is added dropwise, keeping the temperature below 10-15 C. After completion of the addition, the mixture is reacted for 15-20 minutes, afterwards the phases are separated and the aqueous phase is extracted with toluene (250 ml). The cooled combined organic phases are dropped into isopropanol (800 ml) under reflux in about 1 hour. The mixture is refluxed for about 30 minutes and the solution is concentrated to small volume. The resulting oil is taken up into hexane (500 ml) and left under strong stirring for 2-3 hours, the solid is filtered and dried at 50 C. for 16-18 hours. 205 g of a white solid are obtained, in a 78% yield.1H-NMR (300 MHz, D2O, 28 C.): delta 7.00 (broad, 1H exchange with D2O); 4.70 (m, 1H); 3.00 (m, 1H); 2.80 (m, 1H); 2.10 (m, 2H); 1.95 (m, 1H); 1.60 (m, 1H); 1.20-1.00 (m, 8H); 0.80 (d, 6H).

185815-59-2, The synthetic route of 185815-59-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Dipharma Francis S.r.l.; US2009/143615; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.185815-59-2,4-Isobutyldihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

Example 1; Preparation of Fenchyl Ester; A three-neck-flask (0.25 l) was charged with toluene (140 ml), Fenchyl alcohol (9.26 g) and NaH-60% (2.4 g). The mixture was heated to 80 C., and then cooled to 5 C. A solution of 3-isobutyl glutaric anhydride (6.8 g) in toluene (25 ml) was added to the mixture dropwise. The solution was stirred for 3 hours at room temperature. The solvent was evaporated to dryness to obtain the crude ester. The solid was dried at 55 C. under vacuum. Example 2; Isolation of (S), (R)-Fenchyl Ester; The crude ester prepared in example 1, is added to a mixture of ethyl acetate and toluene, and heated to 80 C. (range 400 to 100 C.) until dissolution. The solution is cooled to 2 C. (range 0 to 20 C.) to get a yellowish solid of (S)-3-(1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)carbonyl)methyl)-5-methylhexanoic acid (Fenchyl ester), which is filtered from the mixture.

185815-59-2, As the paragraph descriping shows that 185815-59-2 is playing an increasingly important role.

Reference£º
Patent; Hedvati, Lilach; Gilboa, Eyal; Avhar-Maydan, Sharon; US2007/293694; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.185815-59-2,4-Isobutyldihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

Example 19; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; Methanol (6.2 ml, 153 mmol) was added drop-wise to a 250 ml three-necked, round-bottomed flask equipped with magnetic stirrer and charged with Quinine (7.14 g, 22 mmol), 3-isobutyl glutaric anhydride (3.28 g, 19.3 mmol) and Toluene (100 ml, 30 vol) at -70 C. The reaction was stirred for 17 hours. The solution was concentrated to dryness, and the resulting residue was dissolved in diethyl ether (125 ml). The solution was washed with HCl-2N (40 ml¡Á3). The organic layer was evaporated until dryness, to have 3.7 g yellow oil of R-Hemiester (Optical purity 80%, Yield -95%).

185815-59-2, The synthetic route of 185815-59-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Hedvati, Lilach; Gilboa, Eyal; Avhar-Maydan, Sharon; US2007/293694; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

185815-59-2, 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A three-necked flask equipped with an addition funnel, thermometer pocket, drying tube and a mechanical stirrer, was charged with toluene (400 ml), (S)-(-)-phenylethylamine(142.35 g,1.1764 mole), and 4-dimethylaminopyridine (0.7176 g, 0.0059 mole). The mixture was cooled to a temperature of -10C to -15C, followed by addition of a solution of 3-isobutyl glutaric anhydride (100 g, 0.59 mole) [e.g. obtained in accordance with the process disclosed Drugs of the Future, 24 (8), 862-870 (1999) or according to Example 1 step (A) above] in toluene (100 ml), over a period of 45-60 minutes, and stirring for additional 1.5-2 hours, at a temperature of -10C to -15C. The mixture was then extracted with 10% aqueous solution of NaOH (500 ml), and the aqueous phase was washed with toluene (1×250 ml). The pH of the aqueous phase was adjusted to 2-2.5 by adding a solution of hydrochloric acid (1-12N). The aqueous phase was further extracted with toluene (1x 800 ml) at a temperature of 70-80C. The toluene layer was washed with 10% sodium chloride solution {700ml) at a temperature of 70-80C followed by crystallization to get 125 g (73.0% yield) of a white solid of (3S)-5-methyl-3-(2-oxo-2-{[(1S)-1-phenylethyljamino}ethyl) hexanoic acid with an optical purity of 99.75 %, as measured by chiral HPLC., 185815-59-2

As the paragraph descriping shows that 185815-59-2 is playing an increasingly important role.

Reference£º
Patent; TEVA PHARMACEUTICALS INTERNATIONAL GMBH; JANAGANI, Satyanarayana; (38 pag.)WO2017/19791; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.185815-59-2,4-Isobutyldihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

Example 15: Preparation of r3R)-5-methyl-3-(2-oxo-2(rriR)-l-phenylethvnamino}ethyl) hexanoic acid compound (24); [0089] A three-neck- flask equipped with an addition funnel, thermometer pocket, drying tube and a mechanical stirrer, was charged with n-butanol (100 ml), (R)-(+)- phenylethylamine (35.58 g, 0.147mole) and 4-dimethylaminopyridine (0.18 g, 0.00147 mole). The mixture was cooled to a temperature of 0-50C, followed by addition of a solution of 3-isobutyl glutaric anhydride (25 g, 0.147 mole) in n-butanol (25 ml), over a period of 15-20 minutes, and stirring for additional 1.5-2 hours, at a temperature of 0-50C. The solvent was stripped off and the residue was extracted with 2.5-3 percent aqueous solution of NaOH solution (500 ml), and diluted with water (1000 ml) followed by washing the aqueous phase with toluene (1 x 100 ml and 1 x 50 ml). The pH of the aqueous phase was adjusted to 2-2.5 EPO by adding a 1-12N solution of hydrochloric acid. The aqueous phase was further extracted with ethyl acetate (1 x 150 ml and 1 x 50 ml), followed by drying the combined ethyl acetates extracts over anhydrous sodium sulfate, and stripping off the solvents, to obtain a residue. The residue was crystallized from ethyl acetate and toluene mixture to get 23.1 g (54.03 percent yield) of a white solid of (3R)-5-methyl-3-(2-oxo-2-{[(lR)-l- phenylethyl] amino }ethyl)hexanoic acid with an optical purity of 99.16 percent, as measured by chiral HPLC.

185815-59-2, As the paragraph descriping shows that 185815-59-2 is playing an increasingly important role.

Reference£º
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2007/35789; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.185815-59-2,4-Isobutyldihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

EXAMPLE 14 – SYNTHESIS OF METHYL 3-ISOBUTYL-GLUTARATE (III) A 1 L three-necked round-bottom flask, under nitrogen atmosphere, is added with 3-isobutylglutaric anhydride (50.0 g; 0.290 mol) and methanol (500 ml). The resulting solution is kept under stirring at room temperature for about 16-18 h. After completion of the reaction, the solvent is evaporated off. The title product is obtained as a pale yellow oil, 59.8 g, in 97% yield. 1H-NMR (300 MHz, CDCl3, 28C): delta 3.65 (s, 3H); 2.40 (m, 5H); 1.60 (m, 1H); 1.20 (m, 2H); 0.90 (d, 6H).

185815-59-2, As the paragraph descriping shows that 185815-59-2 is playing an increasingly important role.

Reference£º
Patent; Dipharma Francis S.r.l.; EP1992609; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.185815-59-2,4-Isobutyldihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

General procedure: The N-hydroxy compounds were prepared by the following procedure. 4-substituted anhydride (1 mol) and hydroxylamine hydrochloride (1.14 mol) were suspended in isopropanol (150 mL). A solution of 46% sodium hydroxide solution (3 mol) was added to the mixture was and vigorously stirred for 4 h at 60-65C. The mixture was then acidified to pH 2 by 2 N HCl and extracted with dichloromethane. The dichloromethane layer was evaporated under vacuum the solid thus formed was filtered and recrystallized using methanol., 185815-59-2

The synthetic route of 185815-59-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Ponnusamy, Kannan; Davis Presley; Nagapillai, Prakash; Deivanayagam, Eswaramoorthy; Indian Journal of Heterocyclic Chemistry; vol. 28; 2; (2018); p. 275 – 278;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.185815-59-2,4-Isobutyldihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

Step 4, dilute 3-isobutylglutaric anhydride with methyl tert-butyl ether, add 100 ml of 10% ammonia water in a 500 ml reaction flask, and cool the mixture of 3-isobutylglutaric anhydride after cooling. 80 ml of tert-butyl ether solution, the reaction was stirred at room temperature, and the organic phase was separated, and the pH was adjusted to 0.5-1 with 6 mol/L hydrochloric acid. Washing, decoloring, suction filtration, washing with water, and drying were carried out to obtain (¡À)- 3-carbamoylmethyl-5-methylhexanoic acid;, 185815-59-2

As the paragraph descriping shows that 185815-59-2 is playing an increasingly important role.

Reference£º
Patent; Anhui Dongkai Biological Technology Co., Ltd.; Liu Yaopeng; Yu Zhenyun; Zhou Zhongwei; Wan Qing; Lu Jun; Fu Xuelian; (6 pag.)CN110156732; (2019); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.185815-59-2,4-Isobutyldihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

Example 3(i?)-3-(2-(Cinnamyloxy)-2-oxoethyl)-5-methylhexanoic acid, (III) Procedure BQuinine (28.7g, 88mmol) was suspended in toluene (38OmL). Cinnamyl alcohol (15.5 g, 115mmol) was added and the reaction mixture was cooled to -35 0C. The solution of 3- isobutylglutaric anhydride (15.0 g, 88 mmol) in toluene (1OmL) was added during 15 min and the reaction mixture was stirred at -35 0C for 24 hours. Toluene solution was washed with 5% HCl (250 + 5OmL), and than extracted with 2% K2CO3 solution (1000 + 25OmL). Aqueous extracts were washed with EtOAc (3x10OmL), acidified to pH 1 with cone. HCl and extracted with diisopropylether (150 + 5OmL). Combined extracts were warmed to 35 0C and (S)-alpha- phenylethylamine (9.7 g, 80 mmol) was added, followed by seed crystals (10 mg). Mixture was stirred for 4 hours at 25 C and filtered to obtain 24.8 g of (5)-alpha-phenylethylamine salt of (/?)-3-(2- (cinnamyloxy)-2-oxoethyl)-5-methylhexanoic acid. The salt was suspended in toluene (15OmL) and stirred with 3% HCl (10OmL) until clear solution was obtained. The aqueous acidic solution was separated and organic layer was washed once again with 3% HCl (30 mL). Evaporation of toluene afforded 17.3 g (66%) of monoester as viscous yellowish oil. HPLC analysis on Chiralpak AS column, hexane/EtOH/TFA=95/5/0.1 revealed 90.7 % ee., 185815-59-2

The synthetic route of 185815-59-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PLIVA ISTRAZIVANJE I RAZVOJ D.O.O.; MCLEISH, Nicholas, Alistair, Maxwell; WO2008/9897; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics