Heterocyclic Building Blocks-Oxazolidine

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.

General procedure: n-Butyl lithium (11 mmol, 1.1 eq) was added to a solution of the chiral 4-substituted 1,3-oxazolidin-2-one (10 mmol, 1 eq) in THF (100 mL) at -78 C. After 15 min of stirring at -78 oC, cinnamoyl chloride (11 mmol, 1.1 eq ) was added in dropwise. The mixture was stirred at -78 C for a further 30 min then at 0 C for 15 min, the reaction was quenched with saturated NH4Cl aqueous solution and the resultant slurry was concentrated in vacuo. The residue was diluted with EA and washed with brine. The organic layer was dried over MgSO4, filtered and the solvent removed under reduced pressure to yield the crude product. The crude product was purified by silica flash column chromatography.

As the paragraph descriping shows that 99395-88-7 is playing an increasingly important role.

Reference£º
Article; Zhi, Wubin; Li, Jingya; Zou, Dapeng; Wu, Yangjie; Wu, Yusheng; Tetrahedron Letters; vol. 59; 6; (2018); p. 537 – 540;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

108149-63-9, (R)-tert-Butyl 4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

a) (S)-4-(Benzothiazol-2-ylsulfanyl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester To a stirred, cooled (00C) solution of (R)-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3- carboxylic acid tert-butyl ester (1.36 g; CAS 108149-65-1), 2-mercaptobenzothiazole (1.48 g) and triphenylphosphine (2.32 g) in THF (80 ml) under an argon atmosphere was added diethyl azodicarboxylate (4.1 ml; 40% solution in toluene). The mixture (soon turning to a yellow suspension, slowly warming up to r.t.) was stirred for 18 h overnight, then diluted with EtOAc and washed with sat. aq. Na2CO3. The aqueous phase was back extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (Sitheta2; gradient: cyclohexane -> cyclohexane/EtOAc 85:15) to give (S) -4- (benzothiazol-2-ylsulfanyl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (2.0 g) as light yellow viscous oil.

The synthetic route of 108149-63-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/92785; (2008); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.95715-86-9,Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate,as a common compound, the synthetic route is as follows.

A solution of 3-tert-butyl 4-methyl (4S)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate (10 g, 38.565 mmol, 1.00 equiv), NaBH4 (2.92 g, 77.130 mmol, 2.00 equiv), MeOH (30 mL), and CaCl2 (12.84 g, 115.695 mmol, 3.00 equiv) in THF (150 mL) was stirred for 1 h at RT. The reaction was quenched by the addition of 30 mL of water, extracted with 3¡Á100 mL of EtOAc, dried over anhydrous sodium sulfate and concentrated under vacuum to afford 9.38 g of the title compound as a yellow oil LCMS (ESI, m/z): 232.15 [M+H]+.

The synthetic route of 95715-86-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Ribon Therapeutics Inc.; Vasbinder, Melissa Marie; Schenkel, Laurie B.; Swinger, Kerren Kalai; Kuntz, Kevin Wayne; (410 pag.)US2019/330194; (2019); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

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.

General procedure: n-Butyllithium (1.15mL, 1.0equiv, 2.3M in hexanes) was added to a cooled until -75C solution of the corresponding oxazolidinone (2.6mmol) in anhydrous THF (12mL), then the resulting solution was warmed to -30C and stirred for 20min. At the same temperature, a solution of cinnamoyl chloride (1.0equiv) in anhydrous THF (7mL) was added dropwise and then allowed to rise to at room temperature and left overnight with continuous stirring. After work-up with 10% NH4Cl (15mL), the organic layer was separated and the aqueous layer was extracted with ethyl acetate (2¡Á25ml). The combined organic phase was dried over Na2SO4, filtered and evaporated under reduced pressure. The crude products were purified by chromatography or crystallized from appropriate solvents.

99395-88-7 (S)-4-Phenyloxazolidin-2-one 730424, aoxazolidine compound, is more and more widely used in various.

Reference£º
Article; Leitis, Zigm?rs; L?sis, Viesturs; Tetrahedron Asymmetry; vol. 27; 17-18; (2016); p. 843 – 851;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

2346-26-1, Oxazolidine-2,4-dione is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

WORKING EXAMPLE 16 In substantially the same manner as in Working Example 11, 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-propoxycinnamaldehyde was condensed with 2,4-oxazolidinedione. The condensate was subjected to catalytic hydrogenation to yield 5-[3-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-propoxyphenyl]propyl]-2,4-oxazolidinedione, which was recrystallized from ethyl acetate-ether to give colorless needles, m.p.119-120 C.

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

Reference£º
Patent; Takeda Chemical Industries, Ltd.; US5932601; (1999); A;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

2346-26-1, Oxazolidine-2,4-dione is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

WORKING EXAMPLE 18 A mixture of 2-[5-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]pentyl]-1,3-dioxolan (3.6 g), 2,4-oxazolidinedione (1.7 g), piperidine (0.72 g) and acetic acid (50 ml) was stirred for 16 hours under reflux. The reaction mixture was concentrated under reduced pressure, which was dissolved in ethyl acetate. The solution was successively washed with a saturated aqueous solution of sodium hydrogencarbonate, water, 1N HCl and water, followed by drying (MgSO4). The ethyl acetate layer was concentrated under reduced pressure, which was subjected to column chromatography on silica gel. From the fraction eluted with chloroform-methanol (50:1), was obtained 5-[6-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]hexylidene]-2,4-oxazolidinedione as an oily product. The oily product was dissolved in tetrahydrofuran (THF) (80 ml), to which was added palladium-carbon (5%, 1.0 g). The mixture was subjected to catalytic hydrogenation under 1 atmospheric pressure at room temperature. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The concentrate was subjected to column chromatography on silica gel. From the fraction eluted with chloroform-methanol (50:1), was obtained 5-[6-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]hexyl]-2,4-oxazolidinedione, which was recrystallized from ethyl acetate-isopropyl ether to give colorless prisms, m.p.113-117 C.

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

Reference£º
Patent; Takeda Chemical Industries, Ltd.; US5932601; (1999); A;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1121-83-1,5,5-Dimethyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

The synthesis of 5,5-Dimethyl-oxazolidin-2-one as depicted in the above scheme followed the procedures disclosed in: Bull, S. D.; Davies, S. G.; Jones, S.; Sanganee, H. J. J. Chem. Soc. Perkin Trans. 1 1999, 4, 387.To a 250 mL dry round bottom flask were added 5,5-dimethyl-oxazolidin-2-one (5.10 g, 44.3 mmol), triphosgene (5.26 g, 17.7 mmol) and anhydrous THF (80 mL). The mixture was stirred in an ice-water bath, then triethylamine (8.6 mL, 62.0 mmol) was added slowly. The resulting mixture was stirred at room temperature overnight. The reaction mixture was filtered and the filtrate was concentrated. To the residue was added 2,6-difluoro-4-hydroxybenzaldehyde (5.03 g, 31.9 mmol) and 80 mL of CH2Cl2. The resulting solution was cooled in an ice-water bath, then triethylamine (6.0 mL, 42.5 mmol) was added. After stirring at room temperature for 7 hours, water (100 mL) was added to the reaction mixture. The CH2Cl2 layer was separated, and the aqueous layer was extracted continually with CH2Cl2 (50 mL¡Á3). The combined CH2Cl2 solution was dried over Na2SO4. After removal of the solvent, the residue was purified with a silica gel chromatography (heptane/ethyl acetate, gradient eluting) to give 3,5-difluoro-4-formylphenyl 5,5-dimethyl-2-oxooxazolidine-3-carboxylate (6.9 g) as a pale yellow crystal. Yield: 52%. 1H NMR (CDCl3, 300 MHz): delta=10.39 (s, 1H), 7.09 (d, J=9.0 Hz, 2H), 3.97 (s, 2H), 1.67 (s, 6H).

The synthetic route of 1121-83-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; WARNER CHILCOTT COMPANY, LLC; US2011/98251; (2011); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.90319-52-1,(R)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

Step A: Preparation of (R)-3-cinnamoyl-4-phenyloxazolidin-2-one: A THF (50 mL) solution of (R)-4-phenyloxazolidin-2-one (5.90 g, 36.2 mmol) was cooled to -78 ¡ãC and treated with lithium bis(trimethylsilyl)amide (36.9 mE, 36.9 mmol, 1.0 M in THF) dropwise over 15 minutes. After 15-minute stirring at -78 ¡ãC, a TFTF (10 mL) solution of cinnamoyl chloride (6.33 g, 38.0 mmol) was then introduced. The mixture was stirred for 1 hour at -78 ¡ãC and 2 hours at ambient temperature before it was quenched with saturated NaHCO3 (50 mL) and stirred for 1 hour. The mixture was diluted with EtOAc (200 mL), washed with water and brine, dried over MgSO4, filtered and concentrated to give the product as a pale yellow solid (10.6 g, 99.9percent yield). MS (apci) mlz = 293.9 (M+H).

The synthetic route of 90319-52-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BRANDHUBER, Barbara, J.; KERCHER, Timothy; KOLAKOWSKI, Gabrielle, R.; WINSKI, Sharon, L.; WO2014/78323; (2014); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.90319-52-1,(R)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

Pivaloyl chloride (0.572 g, 4.74 mmol) was added dropwise to a solution of acid 12 (0.500 g, 4.31 mmol) in THF (15mL) at ?20¡ãC. After 1h, 4-(R)-phenyloxazolidinone (13) (2.06g, 12.6 mmol) and LiCl (0.201 g, 4.74 mmol) were added in one portion, and the reaction was warmed to room temperature and stirred overnight. The reaction was diluted with H2O (5mL) and extracted with EtOAc (3¡Á10mL). The combined organic layers were washed with satd aq NaHCO3 (2¡Á5mL), brine (1¡Á5mL), dried (Na2SO3), and concentrated under reduced pressure. The residue was purified via flash column chromatography eluting with hexanes/EtOAc (1:1) to give 0.983 g (87percent) of 14 as a white solid: mp=70?71¡ãC; 1H NMR (CDCl3, 300MHz) delta 7.49 (ddd, J=15.4, 2.0, 2.0Hz, 1H), 7.35 (comp, 5H), 7.07 (ddd, J=15.6, 4.4, 4.4Hz, 1H), 5.51 (dd, J=8.7, 4.1Hz, 1H), 4.73 (dd, J=8.7, 8.7Hz, 1H), 4.30 (dd, J=8.7, 3.8Hz, 1H), 4.14 (dd, J=4.6, 2.0Hz, 2H), 3.42 (s, 3H); 13C NMR (CDCl3, 300MHz) delta 164.4, 153.8, 146.8, 139.3, 129.3, 128.8, 126.2, 120.4, 71.6, 70.2, 58.9, 57.9; MS (CI) m/z 261 [C14H15NO4 (M) requires 261].

The synthetic route of 90319-52-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Hethcox, J. Caleb; Shanahan, Charles S.; Martin, Stephen F.; Tetrahedron; vol. 71; 37; (2015); p. 6361 – 6368;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

99395-88-7, (S)-4-Phenyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To (4S)-4-phenyl-l,3-oxazolidin-2-one (10) (0.405 g, 2.48 mmol, 1 equiv) in DCM (3.00 mL) cooled to 0 C was added a solution of triethyloxonium tetrafluoroborate (1.41 g, 7.44 mmol, 3 equiv) in DCM (3.00 mL). The mixture was allowed to warm slowly to rt and stirred for 18 h. The mixture was diluted with EtOAc (20 mL) and poured slowly over a cooled (0 C) solution of saturated aqueous NaHCC (25 mL). The layers were separated, and the aqueous layer was extracted with EtOAc (2 x 20 mL). The combined organic layers were washed with brine, dried over Na2SC>4, filtered, and concentrated to afford (4S)-2-ethoxy-4-phenyl-4,5- dihydro-l,3-oxazole (17) (0.428 g, 90%): 1HNMR (CDC13) delta: 7.38-7.28 (m, 5H), 5.15 (dd, 1H), 4.47 (dd, 1H), 4.42-4.35 (m, 2H), 4.20 (t, 1H), 1.41 (t, 3H) ppm; MS: (m/e): 192 (M+l).

As the paragraph descriping shows that 99395-88-7 is playing an increasingly important role.

Reference£º
Patent; PURDUE PHARMA L.P.; BLAKE, Paul; TAFESSE, Laykea; (85 pag.)WO2017/192858; (2017); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem