Heterocyclic Building Blocks-Oxazolidine

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

2.2. 1,1-dimethylethyl 4-[(2,4-dioxo-1,3-oxazolidin-3-yl)methyl]piperidine-1-carboxylate A suspension of 13.60 g (46.36 mmol) of 1,1-dimethylethyl 4-{[(methylsulphonyl)oxy]methyl}piperidine-1-carboxylate, prepared in step 2.1., 9.37 g (92.72 mmol) of 1,3-oxazolidine-2,4-dione and 16.02 g (139.08 mmol) of 1,1,3,3-tetramethylguanidine in a mixture of 180 ml of tetrahydrofuran and 30 ml of dimethylformamide is heated at reflux for 24 hours. It is allowed to return to ambient temperature and is concentrated under reduced pressure. The residue is taken up in dichloromethane and water and the aqueous phase is separated off and extracted twice with dichloromethane. The combined organic phases are washed with saturated aqueous sodium chloride solution and dried over sodium sulphate. Following evaporation of the solvent, the residue obtained is purified by chromatography on silica gel, eluding with a 98/2 then 95/5 mixture of dichloromethane and methanol. This gives 12.53 g of product in the form of an orange-brown solid., 2346-26-1

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

Reference£º
Patent; SANOFI-AVENTIS; US2007/21403; (2007); A1;,
Oxazolidine – Wikipedia
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90719-32-7, (S)-4-Benzyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

90719-32-7, Example 3: Preparation of (S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one [Show Image] To a cold suspension (-15 C) of sodium hydride (7.12 g, 178 mmol; ?60% oil suspension) in anhydrous THF (600 mL) (S)-4-benzyloxazolidin-2-one (30.0 g, 169.3 mmol) was added portionwise. The reaction mixture was allowed to reach room temperature during 2 h and stirring was continued for 20 h, after the mixture was recooled to -15 C once more. 3-Methylbutanoyl chloride (23.48 g, 24.00 mL, 194.7 mmol) was added dropwise and the mixture was allowed to reach room temperature during 2 h, and sitirring was continued for additional 3 h. The reaction was quenched by addition of saturated aqueous solution of NaHCO3 (300 mL) and the mixture was stirred at room temperature for 30 min. The product was extracted with CH2Cl2 (3 ¡Á 400 mL). The combined organic layers were washed with saturated aqueous Na2CO3 solution (2 ¡Á 300 mL) and brine (300 mL), and dried over anhydrous Na2SO4. After removal of the solvents under reduced pressure the oily residue was recrystallized from Et2O/petrolether 1:10 (408 mL) to yield, in two crops, 37.19 g (84%) of (S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one as colourless crystals. 1H NMR (300 MHz, CDCl3) delta: 1.03 (d, 3H), 1.04 (d, 3H), 2.24 (m, 1H), 2.75 (dd, 1H) 2.73-2.95 (m, 1H), 3.32 (dd, 1H), 4.14-4.23 (m, 2H), 4.66-4.74 (sym m, 1H), 7.22-7.38 (m, 5H).

As the paragraph descriping shows that 90719-32-7 is playing an increasingly important role.

Reference£º
Patent; Krka Tovarna Zdravil, D.D., Novo Mesto; EP2189442; (2010); A1;,
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95530-58-8, (R)-4-Isopropyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,95530-58-8

Sodium hydride (55% suspension in oil, 144 mg, 3.31 mmol) was added to a solution of (R) -4-isopropyl-2-oxazolidinone (356 mg, 2.75 mmol) in dry tetrahydrofuran (17 mL) under argon atmosphere. The suspension was stirred for 1 hour at rt, then cooled to [0C] and a solution of 1-bromo-3-chloropropane in dry tetrahydrofuran (3 mL) was added dropwise. After 48 h stirring at [58C] the mixture was quenched with water. The solvent was removed by evaporation under reduced pressure and the residue partitioned between water and dichloromethane. The organic layer was evaporated to dryness. Purification of the residue by silica gel column chromatography, eluting with a mixture of ethyl acetate and n-Heptane (70: 30), afforded [(4R)-3- (3-CHLOROPROPYL)-4-ISOPROPYLOXAZOLIDINON-2-ONE] (401 mg, 71 %). A solution of [(4R)-3- (3-CHLOROPROPYL)-4-ISOPROPYLOXAZOLIDINON-2-ONE] (160 mg, 0.78 mmol) in dry DMF (2 mL) was added to a suspension of potassium carbonate (217 mg, 1.57 mmol) and N-(4-fluorobenzyl)-2-(4-isobutoxyphenyl)- N-piperidin-4-yl-acetamide 103NLS56 (250 mg, 0.63 mmol) in dry DMF (6 mL). After addition of sodium iodide (113 mg, 0.75 mmol) the mixture was stirred overnight at [62C] and partitioned between water and dichloromethane. The organic layer were dried over sodium sulphate, filtered and evaporated to dryness. Purification of the residue by silica gel column chromatography, eluting with 5% methanol in dichloromethane, afforded the desired compound (143 mg, 40%). Rf = 0.28 [(MEOH/CH2CL2] 6: 96). LCMS m/z 568 [[M+H] +. IH] NMR (CDCl3, rotamers 0.4 : 0.6) 8 7.20-6. 78 (m, 8H, Ar-H), 4.61-4. 51 (m, 0.6H, pip-H), 4.48 & 4.42 (2s, 2H, benzyl-H), 4.15 (t, 1H, J= 8.8, oxa-H), 4.01 (m, 1H, oxa-H), 3.78-3. 64 (m, 4.2H, pip- H, benzyl-H, oxa-H, CH2OiBu), 3.48 (m, 2.2H, benzyl-H, CONCHCH2), 2.92-2. 79 (m, 3H, pip-H, [CONCH2),] 2.34-2. 22 (m, 2H, [NCH2CH2CH2),] 2.10-1. 96 (m, 3.2H, pip-H, CHiPr, [CHOIBU),] 1.76-1. 50 (m, 6H, pip-H, [NCH2CH2),] 1.32-1. 26 (m, 0.8H, pip-H), 0.99 (m, 6H, [CH3OIBU)] 0.81-0. 87 (m, 6H, [CH3IPR). HPLC TR=] 9.1 min.

As the paragraph descriping shows that 95530-58-8 is playing an increasingly important role.

Reference£º
Patent; ACADIA PHARMACEUTICALS INC.; WO2004/808; (2003); A2;,
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.90719-32-7,(S)-4-Benzyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

90719-32-7, In a 100L reaction kettle connected to an exhaust gas absorption device, add (S)-4-benzyl-2-oxazolidinone (10kg, 56mol), DMAP (catalyst) and xylene (50L), heated to reflux, propionyl chloride (10L, 1V) was added dropwise, and the reaction was refluxed for 2-12 hours after the dropwise addition. HPLC showed that the reaction was complete. Filter and filter cake recovered. The filtrate was concentrated, the concentrated xylene and propionyl chloride mixed solvent was recovered and applied. The concentrated oily liquid was added with 30 L of xylene and 20 L of a saturated sodium bicarbonate solution and stirred for 0.5 h. The liquid was separated, the organic phase was dried, and then used as it was. The feeding method in this step is simple and convenient. During post-processing, catalysts and solvents can be recycled, Compared with the methods described in the existing literature, the present invention has obvious advantages, very suitable for industrial production.

As the paragraph descriping shows that 90719-32-7 is playing an increasingly important role.

Reference£º
Patent; Shanghai Maosheng Kanghui Technology Co., Ltd.; Ding Hailin; Wang Tiantian; Ying Yongcheng; Jiang Xuefeng; Yu Fei; (9 pag.)CN110467530; (2019); A;,
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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,452339-73-0

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.

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

Reference£º
Patent; GLAXO WELLCOME HOUSE; WO2004/37773; (2004); A1;,
Oxazolidine – Wikipedia
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497-25-6, Oxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

497-25-6, General procedure: A Schlenk tube was charged with aryl bromide(1 mmol), oxazolidone(1.2 mmol), N,N-dimethylglycine(10.3mg, 0.1 mmol), recrystallized CuI(9.5mg, 0.05 mmol) and K2CO3(276mg, 2 mmol). The tube was evacuated and backfilled with argon(3 times) before dry DMF(0.5 ml) was added. The reaction mixture was stirred at 120 C until the corresponding aryl bromidewas completely consumed as monitored by TLC. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with H2O and brine, and dried by Na2SO4. Removal of solvent in vacuo and purified by column chromatography on silica gel to provide the desired product.

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

Reference£º
Article; Li, Jiaojiao; Zhang, Yihua; Jiang, Yongwen; Ma, Dawei; Tetrahedron Letters; vol. 53; 31; (2012); p. 3981 – 3983;,
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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

To a solution of oxazolidine-2,4-dione (cas: 2346-26-1, 0.1 g, 0.99 O^N^^BOC mmol) in DMF (5 mL) was added /er/-butyl (2-bromoethyl) carbamate ^ (cas: 39684-80-5, 0.265 g, 1.2 equiv.) and K2CO3 (0.274 g, 2.0 equiv.). The reaction mixture was heated to 70 C for 2 hours. The reaction mixture was then cooled to ambient temperature, and quenched with water (20 mL). The aqueous phase was extracted with EtOAc (3 x 20 mL). The combined organic extracts were washed with water, brine, dried (Na2S04), and concentrated under reduced pressure to afford a residue, which was purified by preparative TLC (Petroleum: EtOAc =1 : 1) to provide carbamate 1-280 as a pale yellow oil (0.1 g, 41 % yield). MS (ESI, pos. ion) m/z: 267(M+Na).

2346-26-1, 2346-26-1 Oxazolidine-2,4-dione 97389, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; CARMOT THERAPEUTICS, INC.; ENQUIST, Johan; KRISHNAN, Shyam; ATWAL, Suman; ERLANSON, Daniel; FUCINI, Raymond V.; HANSEN, Stig; SAWAYAMA, Andrew; SETHOFER, Steven; (719 pag.)WO2019/183577; (2019); A1;,
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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.

General procedure: To a stirred solution of 6 (0.100 g, 0.433 mmol), appropriate substituted phenol (0.649 mmol) and PPh3 (0.182 g,0.693 mmol) in anhydrous toluene (5 mL) was added DIAD(0.14 mL, 0.693 mmol) at 80 C. After 3 h, EtOAc (40 mL)was added to the resulting solution. The organic layer was washed with 0.5 M aqueous NaOH (40 mL) and water (2 X40 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash silica gel column chromatography eluting with Hexanes/EtOAc (9:1) or (95:5) to afford compounds 7a-s.

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

Reference£º
Article; Andrade, Saulo F.; Campos, Edmar F.S.; Teixeira, Claudia S.; Bandeira, Cristiano C.; Lavorato, Stefania N.; Romeiro, Nelilma C.; Bertollo, Caryne M.; Oliveira, Monica C.; Souza-Fagundes, Elaine M.; Alves, Ricardo J.; Medicinal Chemistry; vol. 10; 6; (2014); p. 609 – 618;,
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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

Step b) (E)-5-{3-[3-(5-methyl-2-phenyl-oxazol-4-ylmethyl]-phenyl]-but-2-enyl}-oxazolidine-2,4-dione Tert-butyl lithium (17.5 mL, 29.7 mmol) was added dropwise in to a rapidly stirred cold (-78 C.) solution of lithium chloride (3.6 g, 84.84 mmol) and oxazolidine-2,4-dione (1.43 g, 14.14 mmol) in THF (90 mL). The mixture was stirred at -78 C. for 30 minutes, then gradually warmed to 0 C. After recooling to -78 C., (E)-4-[3-(3-chloro-1-methyl-propenyl)-phenoxymethyl]-5-methyl-2-phenyl-oxazole (5.0 g, 14.14 mmol) in THF (5 mL) was added all at once. After stirring for 10 minutes at -78 C., the mixture was gradually warmed to room temperature, and allowed to stir for 5 hours. Then, the reaction mixture was quenched with aqueous NH4 Cl, poured into water, acidified with HCl, and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography on silica gel (hexane/EtOAc 3/1), gave a white solid (3.5 g, 59% yield, m.p. 138-139 C.). Analysis for: C24 H22 N2 O5 Calc’d: C, 68.89; H, 5.30; N, 6.69 Found: C, 68.49; H, 5.29; N, 6.71, 2346-26-1

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

Reference£º
Patent; American Home Products Corporation; US5468762; (1995); A;; ; Patent; American Home Products Corporation; US5532256; (1996); A;,
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7517-99-9, 5-(Hydroxymethyl)oxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,7517-99-9

General procedure: A Schlenk tube was charged with aryl bromide(1 mmol), oxazolidone(1.2 mmol), N,N-dimethylglycine(10.3mg, 0.1 mmol), recrystallized CuI(9.5mg, 0.05 mmol) and K2CO3(276mg, 2 mmol). The tube was evacuated and backfilled with argon(3 times) before dry DMF(0.5 ml) was added. The reaction mixture was stirred at 120 C until the corresponding aryl bromidewas completely consumed as monitored by TLC. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with H2O and brine, and dried by Na2SO4. Removal of solvent in vacuo and purified by column chromatography on silica gel to provide the desired product.

The synthetic route of 7517-99-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Li, Jiaojiao; Zhang, Yihua; Jiang, Yongwen; Ma, Dawei; Tetrahedron Letters; vol. 53; 31; (2012); p. 3981 – 3983;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem