Heterocyclic Building Blocks-Oxazolidine

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.

E. 3-benzoyl-2-oxazolidinone, VI To a solution of 2-oxazolidinone (4.68 g; 0.05 mol) in 1,2-dichlorethane (60 ml), there is added benzoyl chloride (5.6 ml, 0.05 mol) and triethylamine (7.0 ml; 0.05 mol), with stirring at ambient temperature for 30 mins. The solution is then concentrated at reduced pressure and ethyl acetate is added, thereafter it is filtered to remove the base hydrochloride; the filtrate is partly evaporated and diluted with n-heptane and the precipitated solid is removed by filtration. After washing with water and drying, it gives 3-benzoyl-2-oxazolidinone (5.94 g; 90%). From absolute ethanol it crystallizes in nacar scales with m.p. = 166-170C. A portion of the substance in ethanol, with a catalytic amount of sodium ethoxide at room temperature immediately gives ethyl benzoate and, with aniline, benzanilide.

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Reference£º
Patent; Palomo Coll; Antonio Luis; US3947465; (1976); 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.497-25-6,Oxazolidin-2-one,as a common compound, the synthetic route is as follows.

3-But-3-ynyl-1,3-oxazolidin-2-one (25). A flask was charged with 2-oxazolidinone (1.721 g, 19.17 mmol), tetrabutylammonium bromide (715 mg, 2.20 mmol), potassium carbonate (19.09 g, 138 mmol) and toluene (90 mL). 3-Butynyl-1-tosylate (24) (11.72 g, 52.26 mmol) was added. After the resulting mixture was stirred at 100 C. for 4 h, more tosylate 24 (10.62 g, 47.35 mmol) was added. After stirring overnight, more potassium carbonate (7.52 g, 54.41 mmol) and tosylate 24 (11.94 g, 53.24 mmol) were added. The resulting mixture was stirred at 105 C. for 5.5 h, and potassium carbonate (10.00 g, 72.35 mmol) and tosylate 24 (11.312 g, 50.44 mmol) were added. The mixture was heated at 105 C. overnight, and more tosylate 24 (10.70 g, 47.71 mmol) and potassium carbonate (9.29 g, 67.22 mmol) were added. The mixture was heated to reflux for another 5 h and then cooled to room temperature. Water was added to quench the reaction. The mixture was extracted ethyl acetate (4¡Á200 mL). The organic solution was washed with brine, dried over Na2SO4 and concentrated to afford a residue, which was purified by column chromatography on silica gel (40 g), eluting with EtOAc-hexanes (0-30%), to afford the product 25 as an oil (2.197 g) in 83% yield. IR (KBr film) 3286, 2919, 2118, 1744, 1485, 1429, 1366, 1271, 1236, 1093, 1042, 970, 763 cm-1; 1H NMR (300 MHz, CDCl3) delta 4.32 (t, J=7.8 Hz, 2H), 3.70 (t, J=7.8 Hz, 2H), 3.42 (t, J=6.6 Hz, 2H), 2.45 (dt, J=2.7 Hz, J=6.6 Hz, 2H), 2.00 (t, J=2.7 Hz, 1H); 13C NMR (75 MHz, CDCl3) delta 157.9, 80.6, 70.0, 61.5, 44.5, 42.5, 17.4; ESIMS m/z (rel intensity) 139.98 (100). Anal. (C7H9NO2) C, H, N.

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

Reference£º
Patent; PURDUE RESEARCH FOUNDATION; US2008/300288; (2008); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

452339-73-0, (R)-5-(2,2-Dimethyl-4H-benzo[d][1,3]dioxin-6-yl)oxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 10 Preparation of (R)-3-{6-[2-(2,6-Dichlorobenzyloxy)-ethoxy]-hexyl}-5-(2,2-di methyl-4H-benzo[1,3]dioxin-6-yl)-oxazolidin-2-one (XIII) Potassium tert-butoxide (1.0eqt) was added to a solution of Compound IX (1.0eqt) in DMF (7V) under N2 and the reaction stirred for 1 h at ambient temperature. A solution of compound XII (1.0eqt) in anhydrous DMF (1.5V) was added to the above reaction mass and the reaction allowed stirring at ambient temperature for 3 hr. The reaction mixture was diluted with ice/water and extracted with ethyl acetate. The organic layer was separated then washed successively with water/saturated brine and dried over sodium sulfate. The solution was concentrated to dryness and the residue thus obtained was purified by column chromatography (EtOAc-hexane). The pure fractions were concentrated under vacuum to afford the title compound as pale yellow color oil. Yield: 91%; purity by HPLC: 99.24%; Chiral purity: R-isomer: 99.96%; S-isomer: 0.04%

The synthetic route of 452339-73-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PERRIGO API LTD.; Dammalapati, Venkata Lakshmi Narasimha Rao; Mudduluru, Hari Krishna; Aduri, Ravindra; US2015/239862; (2015); 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.452339-73-0,(R)-5-(2,2-Dimethyl-4H-benzo[d][1,3]dioxin-6-yl)oxazolidin-2-one,as a common compound, the synthetic route is as follows.

Sodium hydride (60% dispersion in oil 1.26 g) was added to a stirred, cooled (ice-bath) solution of (5R)-5-(2, 2-dimethyl-4H-1, 3-benzodioxin-6-yl)-2-oxazolidinone (5.47 g) in dry DMF (50 [ML)] under nitrogen and the mixture was stirred for 15 min at 5 [C.] A solution of 6-bromohexyl [4- (3-IODOPHENYL) BUTYL] ether (10.7 g) in DMF (30 ml) was then added dropwise over 10 min. The mixture was stirred for 2 h at ambient temperature, then poured into aqueous solution of ammonium chloride and extracted into ethyl acetate. The combined extracts were washed with water, dried [(NA2SO4)] and evaporated. The residue was purified on biotage (90 g cartridge) eluting with ether-hexane (3: 2) to give the title compound (9.8 g). LCMS RT= 4.20 min.

As the paragraph descriping shows that 452339-73-0 is playing an increasingly important role.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2004/22547; (2004); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

80-65-9, 3-Aminooxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Following the addition of 4-(4-fluorophenoxy) butyric acid (0.71 g, 3.6 mmol) to 20 mL ofdichloromethane in a 50 mL three-necked round-bottom flask, thesolution was agitated until dissolution. Subsequently, EDCI (0.85 g,4.44 mmol) HOBt (0.6 g, 4.44 mmol) and triethylamine (0.84 g,9.25 mmol) were added in turn at 0 C. Stirring in an ice bath for 1 h,3-amino-2-oxazolidinone (0.37 g, 3.6 mmol) was added again. Thesolutionwas brought to 25 C and stirred overnight. Following TLC,the product was filtered by vacuum and dried under rotary evaporation.The product was a white solid weighing 0.51 g with a yieldof 50.2%.

The synthetic route of 80-65-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Jiang, Kai; Yan, Xinlin; Yu, Jiahao; Xiao, Zijian; Wu, Hao; Zhao, Meihua; Yue, Yuandong; Zhou, Xiaoping; Xiao, Junhai; Lin, Feng; European Journal of Medicinal Chemistry; vol. 194; (2020);,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.80-65-9,3-Aminooxazolidin-2-one,as a common compound, the synthetic route is as follows.

General procedure: Following the addition of 4-(4-fluorophenoxy) butyric acid (0.71 g, 3.6 mmol) to 20 mL ofdichloromethane in a 50 mL three-necked round-bottom flask, thesolution was agitated until dissolution. Subsequently, EDCI (0.85 g,4.44 mmol) HOBt (0.6 g, 4.44 mmol) and triethylamine (0.84 g,9.25 mmol) were added in turn at 0 C. Stirring in an ice bath for 1 h,3-amino-2-oxazolidinone (0.37 g, 3.6 mmol) was added again. Thesolutionwas brought to 25 C and stirred overnight. Following TLC,the product was filtered by vacuum and dried under rotary evaporation.The product was a white solid weighing 0.51 g with a yieldof 50.2%.

As the paragraph descriping shows that 80-65-9 is playing an increasingly important role.

Reference£º
Article; Jiang, Kai; Yan, Xinlin; Yu, Jiahao; Xiao, Zijian; Wu, Hao; Zhao, Meihua; Yue, Yuandong; Zhou, Xiaoping; Xiao, Junhai; Lin, Feng; European Journal of Medicinal Chemistry; vol. 194; (2020);,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2346-26-1,Oxazolidine-2,4-dione,as a common compound, the synthetic route is as follows.

A solution of 1.0 g (4.20 mmol) of 2-[4-(1H-pyrrolo[2,3-b]pyridin-1-yl)phenyl]ethanol, prepared in step 13.1., 0.51 g (5.04 mmol) of 1,3-oxazolidine-2,4-dione and 1.21 g (4.62 mmol) of triphenylphosphine in 16 ml of tetrahydrofuran, cooled by a bath of acetone and ice, is admixed dropwise with 0.84 g (4.2 mmol) of diisopropyl azodicarboxylate in solution in 2 ml of tetrahydrofuran. The mixture is subsequently heated to ambient temperature again and stirred overnight. 4 g of silica are added and the mixture is evaporated to dryness. The residue is purified by chromatography on silica gel, eluting with a 70/30 then 60/40 then 50/50 and 40/60 mixture of cyclohexane and ethyl acetate, to give 1.52 g of product in the form of a sticky solid, which is used as it is in the following step

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

Reference£º
Patent; Sanofi-Aventis; US2006/14830; (2006); A1;,
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

Step 4. (5)-3-((5)-3-(4-Chlorophenyl)-3-(5-(trifluoromethyl)pyridin-3-yl)propanoyl)-4- phenyloxazolidin-2-one To a precooled (0 C) solution of (5)-3-(4-chlorophenyl)-3-(5- (trifluoromethyl)pyridin-3-yl)acrylicacid (1.30 g, 3.94 mmol) in THF (10.0 mL) was added pivolyl chloride (570 mg, 4.73 mmol), DMAP (cat), followed by triethylamine (796 mg, 7.88 mmol) and stirred for 1 h. In another precooled (0 C) suspension of 60% NaH (7.88 mmol) in THF, was added (5)-4-phenyloxazolidin-2-one (772 mg, 4.73 mmol) in THF (10.0 mL) drop- wise and stirred at 0 C for 1 h. The mixed anhydride was added to the reaction mixture and stirred for another 5 h. The reaction mixture was quenched with water (20.0 mL) and extracted with EtOAc (2 x 100 mL). The combined EtOAc extracts were washed with brine (100 mL), dried ( a2S04), filtered, and concentrated under reduced pressure. The residue was purified on 12 g S1O2 using a gradient elution of 0-20% EtOAc in hexanes. Fractions containing the product were combined and concentrated under reduced pressure to provide the product (1.40 g, 76%) as a white solid. MS: m/z = 475 (M+H+).

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

Reference£º
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO. LTD.; WILLIAMS, Peter, D.; MCCAULEY, John, A.; BENNETT, David, J.; BUNGARD, Christopher, J.; CHANG, Lehua; CHU, Xin-Jie; DWYER, Michael, P.; HOLLOWAY, M. Katherine; KEERTIKAR, Kartik, M.; LOUGHRAN, H. Marie; MANIKOWSKI, Jesse, J.; MORRIELLO, Gregori, J.; SHEN, Dong-Ming; SHERER, Edward, C.; SCHULZ, Jurgen; WADDELL, Sherman Tim; WISCOUNT, Catherine, M.; ZORN, Nicolas; SATYANARAYANA, Tummanapalli; VIJAYASARADHI, Sivalenka; HU, Bin; JI, Tao; ZHONG, Bin; WO2015/17393; (2015); A2;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

160695-26-1, (R)-4-Phenyl-3-propionyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of 16a (22.4 g, 96.0 mmol) in THF (300 mL) cooled to -78 C was added NaHMDS (100 mL, 100 mmol, 1.0 M solution in THF) dropwise over 20 min. The reaction was stirred at -78 C for an additional hour before the dropwise addition of allyl iodide (8.78 mL, 96.0 mmol) over 10 min. The reaction was stirred for an additional 5 hr at -78 C before the cooling bath was removed and the reaction was quenched with the addition of sat. NH4Cl. The layers were separated, and the aqueous layer was washed with Et2O x 3. The combined organic material was washed with sat. Na2S2O3, dried over MgSO4, filtered, concentrated, and purified via flash chromatography (Teledyne ISCO flash chromatography system; silica gel column; 9:1Hexane:EtOAc) to afford the desired product as a colorless oil (14.9 g, 58% yield). Spectral data were in accordance with reported literature values.5

As the paragraph descriping shows that 160695-26-1 is playing an increasingly important role.

Reference£º
Article; Reed, Carson W.; Fulton, Mark G.; Nance, Kellie D.; Lindsley, Craig W.; Tetrahedron Letters; vol. 60; 10; (2019); p. 743 – 745;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

497-25-6, Oxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 90:3-[2-({6-[(trans-4-hydroxycyclohexyl)amino]-4-[(2-methyl-1 H-imidazol-1 -yl)methyl]-2- pyridinyl}amino)-1 ,3-benzothiazol-6-yl]-1 ,3-oxazolidin-2-oneUnder an atmosphere of nitrogen, a mixture of trans-4-({6-[(6-bromo-1 ,3-benzothiazol-2- yl)amino]-4-[(2-methyl-1 H-imidazol-1 -yl)methyl]-2-pyridinyl}amino)cyclohexanol [example 79] (150mg, 0.29mmol), 1 ,3-oxazolidin-2-one (76mg, 0.88mmol), caesium carbonate (286mg, 0.88mmol) and copper(l) iodide (167mg, 0.88mmol) in dry N,N- dimethylformamide (3mL) was thoroughly degassed by the repeated alternate application of vacuum and nitrogen pressure, then treated with N,N’-dimethylethylenediamine (0.125ml_, 1.17mmol) and the mixture was heated at 1 10C for 1 hour. The mixture was cooled to ambient temperature, filtered and evaporated to dryness. The product was subjected to purification by mass-directed automated preparative HPLC (formic acid modifier) to afford the title compound (122mg, 0.24mmol, 80% yield). LCMS (Method A): Rt 0.59 minutes; m/z 520 (MH+)

As the paragraph descriping shows that 497-25-6 is playing an increasingly important role.

Reference£º
Patent; GLAXO GROUP LIMITED; ALDER, Catherine Mary; BALDWIN, Ian Robert; BARTON, Nicholas Paul; CAMPBELL, Amanda Jennifer; CHAMPIGNY, Aurelie Cecile; HARLING, John David; MAXWELL, Aoife Caitriona; SIMPSON, Juliet Kay; SMITH, Ian Edward David; TAME, Christopher John; WILSON, Caroline; WOOLVEN, James Michael; WO2011/110575; (2011); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem