Category: 185815-59-2

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 – SYNTHESIS OF METHYL (S)-3-ISOBUTYL-GLUTARATE (III) A 1 L three-necked round-bottom flask, under nitrogen atmosphere, is loaded with 3-isobutylglutaric anhydride (5.0 g; 29 mmol) of formula (II) and methyl isobutyl ether (MTBE) (100 ml). The resulting solution, kept at temperatures of about 20-25C, is added with methanol (2.5 g) and CAL-B Novozym 435 (2.5 g), and the solution is kept under stirring for about 3 h. After that, the enzyme is filtered off and the solvent is evaporated off. The resulting product has 85% enantiomeric purity.

185815-59-2, 185815-59-2 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione 11480690, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Dipharma Francis S.r.l.; EP1992609; (2008); 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

Example 1: Preparation of (3R)-5-methyl-3-r2-oxo-2{rdR)-l-phenylethyl]amino|ethyl) hexanoic acid compound (24*); [0075] A three-necked flask equipped with an addition funnel, thermometer pocket , drying tube and a mechanical stirrer, was charged with toluene (400 ml), (R)-(+)- EPO phenylethylamine (38.59 g, 0.0.319 mole) and 4-dim’ethylaminopyridine (0.358 g, 0.0029 mole). The mixture was cooled to a temperature of -50C to -60C, followed by addition of a solution of 3-isobutyl glutaric anhydride (50 g, 0.294 mole) in toluene (100 ml), over a period of 45-60 minutes, and stirring for additional 1.5-2 hours, at a temperature of -50C to -60C. The mixture was then extracted with 3.5-4.0 percent aqueous solution of NaOH (1000 ml), and the aqueous phase was washed with toluene (1 x 250 ml). The pH of the aqueous phase was adjusted to 2-2.5 by adding a solution hydrochloric acid (1-12N). The aqueous phase was further extracted with ethyl acetate (1 x 300 ml and 1 x 100 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 66 g (77.2 percent yield) of a white solid of (3R)-5-methyl-3-(2-oxo-2-{[(lR)- 1-phenylethyl] amino} ethyl) hexanoic acid with an optical purity of 99.91 percent, as measured by chiral HPLC.; Example 12: Preparation of r3RV5-me1hyl-3-f2-oxo-2(rriRVl-phenyle1hyl1ainino)ethyl’) hexanoic acid compound (24*); [0086] A three-necked flask equipped with an addition funnel, thermometer pocket, drying tube and a mechanical stirrer, was charged with toluene (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 0-5C, followed by addition of a solution of 3-isobutyl glutaric anhydride (25 g, 0.147 mole) in toluene (25 ml), over a period of 15-20 minutes, and stirring for additional 1.5-2 hours, at a temperature of 0-5 C. The mixture was then extracted with 2.5-3 percent aqueous solution of NaOH solution (500 ml), and the aqueous phase was washed with toluene (1 x 50 ml). The pH of the aqueous phase was adjusted to 2-2.5 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 29.3 g (68.5 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 99.34 percent, as measured by chiral HPLC., 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; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2007/35789; (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

Example 2 (i?)-3-(2-(Cinnamyloxy)-2-oxoethyl)-5-methylhexanoic acid, (III) Procedure AQuinine (28.7g, 88 mmol) was suspended in toluene (380 mL). Cinnamyl alcohol (15.5 g, 115 mmol) was added and the reaction mixture was cooled to -35 0C. The solution of 3- isobutylglutaric anhydride (15.0 g, 88 mmol) in toluene (10 mL) was added during 15 min and the reaction mixture was stirred at -35 C for 24 hours. Toluene solution was washed with 5% HCl (250 mL) and evaporated. Oily residue was dissolved in 2-PrOH (300 mL), warmed to 45 0C, and the solution of 1-adamantylamine (12.0 g, 79 mmol) in MTBE (100 mL) was added. The mixture was stirred at 25 0C for 6 hours, filtered, washed with 2-PrOH (100 mL) and dried under reduced pressure to yield 28.1 g of 1-adamantylamine salt of (/?)-3-(2-(cinnamyloxy)-2-oxoethyl)-5- methylhexanoic acid. The salt was suspended in toluene (15OmL) and stirred with 3% HCl (100 mL) until a clear solution was obtained. Aqueous acidic solution was separated and organic layer was washed once again with 3% HCl (3OmL). Evaporation of toluene afforded 18.1 g (69%) of monoester as viscous yellowish oil. HPLC analysis on Chiralpak AS column, hexane/EtOH/TFA=95/5/0.1 revealed 91.2 % ee. 1H NMR (CDCl3), delta/ppm: 0.87 (d, 6H, J=6.5 Hz), 1.21-1.27 (m, 2H), 1.56-1.70 (m, IH), 2.38-2.48 (m, 5H), 4.73 (dd, 2H, J/=6.5 Hz, J2=1.2 Hz), 6.27 (dt, IH J/=15.8 Hz, J2=6.5 Hz), 6.65 (d, IH, J=I 5.8 HZ), 7.22-7.40 (m, 2H).13C NMR (CDCl3), delta/ppm: 22.34, 25.07, 29.64, 38.30, 38.48, 43.26, 64.92, 122.95, 126.50, 127.96, 128.49, 134.18, 136.07, 172.26, 178.64., 185815-59-2

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

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

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 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 -5C. 3-Isobutyl-glutaric anhydride (183.0 g, 1.075 mol) is dropped therein in about 1-2h, keeping the temperature below 0-5C and the mixture is reacted for about 1h. 35-37% Hydrochloric acid (450 ml) and toluene (400 ml) are added. Keeping a temperature of -5C, a solution of sodium nitrite (160.0 g, 2.026 mol) in water (320 ml) is added dropwise, keeping the temperature below 10-15C. 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 50C for 16-18 hours. 205 g of a white solid are obtained, in a 78% yield. 1H-NMR (300 MHz, D2O, 28C): 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 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione 11480690, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Dipharma Francis S.r.l.; EP2067768; (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 3: Preparation of (3RV5-methyl-3-r2-oxo-2{r(lR)-l-phenylethyl1ammo|ethvD hexanoic acid compound (24); [0077] A three-necked flask equipped with an addition funnel, thermometer pocket, drying tube and a mechanical stirrer, was charged with toluene (100 ml), (R)-(H-)- phenylethylamine (35.58 g, 0.294 mole) and 4-dimethylaminopyridme (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 toluene (25 ml), over a period of 15-20 minutes, and stirring for additional 1.5-2 hours, at a temperature of 0-5C. The mixture was then extracted with 2.5-3.0 percent aqueous solution OfNaHCO3 solution (500 ml), and the aqueous phase was washed with toluene (1 x 100 ml). The pH of the aqueous phase was adjusted to 2-2.5 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 28.4g (66.4 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 99.6 percent, as measured by chiral HPLC.

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

Reference£º
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2007/35789; (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

Example 14: Preparation of GRV5-methyl-3-f2-oxo-2(r(lR)-l-rhohenylethvnamino>ethvD hexanoic acid compound (24); [0088] A three-necked flask equipped with an addition funnel, thermometer pocket, drying tube and a mechanical stirrer, was charged with ethanol (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 0-5 C, followed by addition of a solution of 3-isobutyl glutaric anhydride (25 g, 0.147 mole) in ethanol (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 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 22.7 g (53.09 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 99.17 percent, as measured by chiral HPLC.

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

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