Heterocyclic Building Blocks-Oxazolidine

695-53-4, 5,5-Dimethyloxazolidine-2,4-dione is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 125(3R*,4R*)-N-[3,5-bis(trifluoromethyl)benzyl]-1-[3-(5,5-dimethyl-2,4-dioxo-1,3-oxazolidin-3-yl)propyl]-3-(4-fluoro-2-methylphenyl)-N-methylpiperidine-4-carboxamide monohydrochloride(step 1)To a solution of 5,5-dimethyl-1,3-oxazolidine-2,4-dione (500 mg) in DMF (10 mL) was added NaH (186 mg) at room temperature, and the mixture was stirred for 5 min. 1-Bromo-3-chloropropane (508 muL) was further added, and the mixture was stirred at room temperature for 4 days. The reaction mixture was concentrated under reduced pressure, and ethyl acetate was added to the residue. The organic layer was washed with aqueous citric acid solution and water and dried, and the solvent was evaporated under reduced pressure to give crude 3-(3-chloropropyl)-5,5-dimethyl-1,3-oxazolidine-2,4-dione as a colorless oil.

695-53-4 5,5-Dimethyloxazolidine-2,4-dione 3081, aoxazolidine compound, is more and more widely used in various.

Reference£º
Patent; Shirai, Junya; Morimoto, Shinji; Sugiyama, Hideyuki; Sakauchi, Nobuki; Yoshikawa, Takeshi; US2008/275085; (2008); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.875444-08-9,(4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

(45,5i?)-5-[3,5-w(trifluoromethyl)phenyl]-4-methyl-l,3-oxazolidin-2-one (Intermediate 17, 400 mg, 1.28 mmol) was treated with NaH (60% in oil, 128 mg, 3.2 mmol) and 2-(bromomethyl)-l-iodo-4- (trifluoromethyl)benzene (Intermediate 11, 466 mg, 1,28 mmol). The reaction was stirred at room temperature for 18 h. The reaction was quenched with H2O (1 mL) and partitioned between EtOAc (80 mL) and H2O (25 mL). The aqueous phase was re-extracted with EtOAc (2 x 20 mL) and the combined organic extracts were washed with brine (30 mL), dried (MgStheta4) and concentrated in vacuo to give the crude product. This was purified by flash silica-gel chromatography (0-30% EtOAc in hexanes gradient) to afford (4S’,5i?)-5-[3,5-/5(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]-4-methyl-l,3- oxazolidin-2-one as a white solid. LCMS = 598.0 (M+l)+. lH NMR (CDCI3, 500 MHz): delta 8.06 (d, J =8.2 Hz, 1 H)3 7.93 (s, 1 H), 7.82 (s, 2 H), 7.61 (s, 1 H), 7.33 (dd, J= 8.2, 1.4 Hz, 1 H), 5.79 (d, J= 7.8 hz, 1 H), 4.91 (d, J= 16 Hz, 1 H)54.40 (d, J= 16 Hz, 1 H), 4.16-4.06 (m, 1 H), 0.83 (d, J= 6.4 Hz, 3 H).

As the paragraph descriping shows that 875444-08-9 is playing an increasingly important role.

Reference£º
Patent; MERCK & CO., INC.; WO2007/81571; (2007); A2;,
Oxazolidine – Wikipedia
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2346-26-1, Oxazolidine-2,4-dione is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Into a 100 mL three neck round-bottom flask, were placed oxazolidine-2,4-dione (515 mg, 5.096 mmol, 1 equiv.), LiCl (648 mg, 15.3 mmol, 3 equiv.) and THF (30 mL). The reaction was purged with an inert atmosphere of nitrogen. The mixture was then added t-BuLi (9.6 mL, 15.3 mmol, 1.6M) dropwise with stirring at -78 C. The resulting solution was stirred for 30 min at -78. 1-(6-(8-Fluoronaphthalen-2-yl)-2-methoxypyridin-3-yl)-2-methylpropan-1-one (500 mg, 1.546 mmol, 0.3 equiv.)/THF (3 mL) was added to above solution at -78 C. The resulting solution was stirred for 30 min at -78 C. and 1 hrs at room temperature. The reaction progress was monitored by TLC/LCMS (DCM/MeOH=20:1). The reaction was then quenched by the addition of 3 mL of NH4Cl (aquous). The reaction was extracted with ethyl acetate and concentrated under vacuum. The residue was applied onto a silica gel column with DCM/MeOH (5:95) to yield 5-(1-(6-(8-fluoronaphthalen-2-yl)-2-methoxypyridin-3-yl)-1-hydroxy-2-methylpropyl)oxazolidine-2,4-dione as a white solid. Mass spectrum (ESI, m/z): Calculated for C23H21FN2O5, 425.1 (M+H), found 425.1.

As the paragraph descriping shows that 2346-26-1 is playing an increasingly important role.

Reference£º
Patent; Janssen Pharmaceutica NV; Zhang, Xuqing; Macielag, Mark J.; (181 pag.)US2019/47961; (2019); A1;,
Oxazolidine – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.108149-63-9,(R)-tert-Butyl 4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate,as a common compound, the synthetic route is as follows.

a) A solution of 10.7 g of t-butyl (R)-4-hydroxymethyl-2,2-dimethyl-3-oxazolidinecarboxylate (J. Org. Chem. 52, 1987, 2361-64) in 107 ml of pyridine is treated with 9.7 g of p-toluenesulphonyl chloride. The reaction mixture is stirred for 17 hours, then taken up in ethyl acetate and washed with water. After drying and evaporation the residue is purified over silica gel with hexane/ethyl acetate (3:1). There are obtained 15.1 g of t-butyl (S)-2,2-dimethyl-4-(p-tolylsulfonyloxymethyl)-3-oxazolidinecarboxylate.

As the paragraph descriping shows that 108149-63-9 is playing an increasingly important role.

Reference£º
Patent; Hofmann-La Roche Inc.; US5260307; (1993); A;,
Oxazolidine – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.497-25-6,Oxazolidin-2-one,as a common compound, the synthetic route is as follows.

To a solution of A-D (12 mmol) in H2O (5 mL) was added NaOH (15 mmol). To this was then added acetone (45 mL), followed by the addition of the corresponding acyl chloride (15 mmol). The mixture was stirred for 30 min at RT. Acetone was removed from solution under reduced pressure and the remaining aqueous solution was further diluted with H2O (20 mL). This was then extracted with EtOAc (3¡Á20 mL). The organic phases were combined and dried with MgSO4, concentrated, then purified via silica gel chromatography eluting hexanes and EtOAc.

The synthetic route of 497-25-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Cohen, Seth M.; Monserrat, Jean-Philippe; Perez, Christian; US2015/5352; (2015); A1;,
Oxazolidine – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.16251-45-9,(4S,5R)-4-Methyl-5-phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

Example 32e (4S,5R)-3-(Bromoacetyl)-4-methyl-5-phenyloxazolidin-2-one 82 ml of a 2.5 molar solution of butyllithium in hexane is added to a solution of 33.06 g (186.6 mmol) of (4S,5R)-4-methyl-5-phenyloxazolidin-2-one in 500 ml of tetrahydrofuran within 30 minutes at -70 C. under argon. Then, a solution of 15.55 ml (187 mmol) of bromoacetyl chloride in 250 ml of tetrahydrofuran is added in drops in such a way that the internal temperature does not exceed -65 C. Then, it is stirred for one more hour at -70 C. Then, the reaction mixture is poured onto 50 ml of saturated aqueous ammonium chloride solution. 90 ml of saturated aqueous sodium bicarbonate solution is then added, allowed to come to 25 C., diluted with water and extracted with ethyl acetate. The organic phase is washed with saturated aqueous sodium chloride solution, dried on sodium sulfate and chromatographed on silica gel. 42.32 g (76%) of the title compound is obtained. 1H-NMR (CDCl3): delta=0.95 (3H), 4.57 (2H), 4.80 (1H), 5.76 (1H), 7.2-7.5 (5H) ppm.

The synthetic route of 16251-45-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; KLAR, ULRICH; SCHWEDE, WOLFGANG; SKUBALLA, WERNER; BUCHMANN, BERND; US2003/144523; (2003); A1;,
Oxazolidine – Wikipedia
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2346-26-1, Oxazolidine-2,4-dione is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 1.0 g (4.02 mmol) of 2-(4-[(4-chlorophenyl)oxy]phenyl)ethanol, prepared in accordance with Example 14.1., and 1.1 ml (7.89 mmol) of triethylamine in 12 ml of dichloromethane, cooled by an ice bath, is admixed with a solution of 0.60 g (5.24 mmol) of methanesulphonyl chloride in 2 ml of dichloromethane. The combined solutions are subsequently stirred at ambient temperature for 2 hours. They are diluted with 25 ml of water and 75 ml of dichloromethane. After the phases have settled and been separated, the organic phase is washed with 25 ml of water then 25 ml of saturated aqueous sodium chloride solution, dried over sodium sulphate and evaporated to dryness, to give 1.32 g of product in the form of an oil. The product is redissolved in 12 ml of tetrahydrofuran. 0.50 g (5 mmol) of 1,3-oxazolidine-2,4-dione and a solution of 0.92 g (8.0 mmol) of 1,1,3,3-tetramethylguanidine in solution in 4 ml of tetrahydrofuran are added. The mixture is subsequently heated at reflux overnight. It is cooled with an ice bath and 25 ml of an aqueous 0.1N solution of hydrochloric acid and 100 ml of ethyl acetate are added. After the phases have settled, the organic phase is separated off and washed with two times 25 ml of water then with 25 ml of saturated aqueous sodium chloride solution, dried over sodium sulphate and evaporated to dryness. The residue is purified by chromatography on silica gel, eluting with an 85/15 then 75/25 and 65/35 mixture of cyclohexane and ethyl acetate, to give 1.20 g of product in the form of a white solid. Melting point ( C.): 105-107

The synthetic route of 2346-26-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Sanofi-Aventis; US2006/14830; (2006); A1;,
Oxazolidine – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.99395-88-7,(S)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

The compound of formula II (250 g, 1.53 mol) was added to toluene (3750 mL)Heat to 70 degrees. Sodium methoxide methanol solution (29 wt%, 314 g, 1.68 mol) was added dropwise.Plus End, atmospheric distillation of methanol. Cooled to 0-5 C,The compound of formula III (364.4 g, 1.68 mol)Temperature is not higher than 20 . Add finished, the reaction 1-2 hours.After the reaction was completed, water (250 mL) was added, heated to 50-60 C, allowed to stand for delamination and the aqueous phase was separated.The organic phase is washed twice with water. The organic phase was concentrated to give the crude product.The crude product was beaten with n-hexane (1500 mL), filtered and dried to obtain the intermediate of formula IV.Yield: 436g, yield: 95.4%

The synthetic route of 99395-88-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; (11 pag.)CN107573304; (2018); A;,
Oxazolidine – Wikipedia
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95715-86-9, Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of LiOH (0.046 g, 1.928 mmol) in water (2 mL) was added to a solution of (S)-3-tert-butyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate (0.5 g, 1.928 mmol) in THF (6 mL). The resulting mixture was stirred at rt for 48 h, acidified to pH 4 with a 1 N aqueous solution of hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases were dried (MgS04), filtered and concentrated under vacuum to afford Cap L-25 (0.2 g) as a yellow oil. Used without further purification.XH NMR (400MHz, DMSO-d6, mixture of rotomers) delta 12.72 (br. s., 1H), 4.33 – 4.23 (m, 1H), 4.18 – 4.09 (m, 1H), 3.93 (dt, J=9.0, 3.3 Hz, 1H), 1.56 – 1.51 (m, 3H), 1.42 (s, 7H), 1.39 – 1.33 (m, 6H);13C MR (101MHz, DMSO-d6, mixture of rotomers) delta 172.32 – 171.83 (m), 150.7, 93.76 – 93.42 (m), 79.66 – 79.01 (m), 65.94 – 65.54 (m), 58.79 – 58.57 (m), 28.05 – 27.74 (m, 3C), 24.93 – 24.75 (m), 24.16 – 23.99 (m)

As the paragraph descriping shows that 95715-86-9 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (2015); A1;,
Oxazolidine – Wikipedia
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17016-83-0, (S)-4-Isopropyl-2-oxazolidinone is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0061] An oven-dried 500 milliliter (mL) Schlenk flask was cooled under nitrogen gas (N2)and then charged with (S)-4-isopropyloxazolidin-2-one (7.05 grams (g), 54.6 millimoles (mmol))and anhydrous THF (300 mL). After sealing with a rubber septum, the resulting colorless solutionwas cooled to -78 C in a dry ice/acetone bath and treated with a solution of n-BuLi (2.5 Molar (M)in hexanes , 24.0 mL, 60.0 mmol). The reaction mixture was stirred at -78 C for 30 minutes (mm)and treated with via syringe with 3-phenylpropanyl chloride (8.80 mL, 59.2 mmol). The resultingyellow solution was stirred for 2.5 hours (h) at -78 C, the cold bath was removed, a solution of saturated aqueous ammonium chloride (NH4C1, 100 mL) was added, and the resulting white suspension was allowed to stir at room temperature for 10 mm. The crude reaction mixture was extracted with ethyl acetate (EtOAc, 3 xl 00 mL), and the combined organic extracts were washed with saturated aqueous sodium chloride solution (NaC1, brine, 100 mL), dried over anhydrous sodium sulfate (Na2SO4), filtered, and concentrated by rotary evaporation. The crude concentrate was purified via column chromatography (silica gel (Si02), 1-30% acetone in hexanes) to give the title compound (11.4 g, 80%) as a white solid: mp 59 – 62 C; ?H NMR (400 MHz, CDC13) oe 7.33 -7.16 (m, 5H), 4.44-4.39 (m, 1H), 4.24 (dd,J= 9.1, 8.1 Hz, 1H), 4.19 (dd, J= 9.1, 3.2 Hz, 1H),3.32 (ddd, J= 16.9, 8.6, 6.7 Hz, 1H), 3.22 (ddd, J= 16.9, 8.0, 7.2 Hz, 1H), 3.06 – 2.92 (m, 2H),2.35 (pd, J= 7.0, 3.9 Hz, 1H), 0.90 (d, J= 7.0 Hz, 2H), 0.84 (d, J= 7.0 Hz, 2H); ?3C NMR (101MHz, CDC13) oe 172.40, 154.06, 140.49, 128.56, 128.46, 126.24, 63.40, 58.45, 37.07, 30.45, 28.39,17.97, 14.64; ESIMS m/z 262 ([M+H]j.

As the paragraph descriping shows that 17016-83-0 is playing an increasingly important role.

Reference£º
Patent; DOW AGROSCIENCES LLC; BOEBEL, Timothy A.; LU, Yu; MEYER, Kevin G.; YAO, Chenglin; DAEUBLE, John F.; BRAVO-ALTAMIRANO, Karla; NUGENT, Benjamin M.; (237 pag.)WO2016/7529; (2016); A1;,
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