Heterocyclic Building Blocks-Oxazolidine

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

Example 64N-{6-chloro-4,4-dimethyl-2-[3-(2-oxo-oxazolidin-3-yl)-phenyl]-l,2,3,4-tetrahydro- quinoline-8-carbonyl}-methanesulfonamide A mixture of 2-(3-bromo-phenyl)-6-chloro-4,4-dimethyl-l,2,3,4-tetrariydro-quinoline-8- carboxylic acid methyl ester (1 g, 2.5 mmol), oxazolidin-2-one (230 mg, 2.63 mmol), copper(I) iodide (95 mg, 0.5 mmol), N,N’-dimethyl-ethane-l,2-diamine (0.11 mL, 1 mmol), and potassium carbonate (1.04 g, 7.5 mmol) in dimethyl sulfoxide (10 mL). The reaction mixture was stirred at 120C for 16 h. Then the reaction mixture cooled to room temperature. The reaction mixture was extracted with ethyl acetate (2 x 50 mL), washed with water (2 x 20 mL) and saturated aqueous ammonium chloride solution (2 x 20 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by Waters automated flash system (column: Xterra 30 mm x 100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 6-chloro-4,4-dimethyl-2-[3-(2-oxo-oxazolidin-3- yl)-phenyl]-l,2,3,4-tetrahydro-quinoline-8-carboxylic acid (0.8 g, 80%) as a white solid: MS(ESI) M+1 = 400.1.To a suspension of methanesulfonamide (665 mg, 7 mmol) in N,N-dimethylformamide (3 mL) was added sodium hydride (280 mg, 7 mmol). The resulting mixture was stirred at 25C for 1 h to afford Solution A64. A solution of 6-chloro-4,4-dimethyl-2-[3-(2-oxo- oxazolidin-3-yl)-phenyl]-l,2,3,4-tetrahydro-quinoline-8-carboxylic acid (400 mg, 1 mmol) and Iota,Gamma-carbonyldiimidazole (325 mg, 2 mmol) in N,N-dimethylformamide (2 mL) was stirred at 70C for 1 h and cooled to room temperature to afford Solution B64. Solution B64 was added to Solution A64 and the resulting mixture was stirred at 25C for 1 h. To the reaction mixture was added water (0.5 mL). The mixture was filtered to remove the insoluble solid, and the filtrate was purified by Waters automated flash system (column: Xterra 30 mm x 100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded N- { 6-chloro-4,4-dimethyl-2-[3-(2-oxo-oxazolidin-3-yl)-phenyl]-l,2,3,4-tetrahydro-quinoline- 8-carbonyl}-methanesulfonamide (37 mg, 7%) as a white solid: MS(ESI) M+l = 478.0., 497-25-6

Big data shows that 497-25-6 is playing an increasingly important role.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; FENG, Lichun; HUANG, Mengwei; LIU, Yongfu; WU, Guolong; YAN, Shixiang; YUN, Hongying; ZHOU, Mingwei; WO2012/101068; (2012); 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.17016-83-0,(S)-4-Isopropyl-2-oxazolidinone,as a common compound, the synthetic route is as follows.

Intermediate S-i H: (4S)-4-(Propan-2-yl)-3 -(5,5,5 -trifluoropentanoyl)- 1,3 -oxazolidin-2- one[00146j To a stirred solution of 5,5,5-trifluoropentanoic acid (5.04 g, 32.3 mmol) in DCM (50 mL) and DMF (3 drops) was added oxalyl chloride (3.4 mL, 38.8 mmol) dropwise over 5 mm and the solution was stirred until all bubbling subsided. The reaction mixture was concentrated under reduced pressure to give pale yellow oil. To a separate flask charged with a solution of (4S)-4-(propan-2-yl)- 1 ,3-oxazolidin-2-one (4.18g, 32.4 mmol) in THF (100 mL) at -78 C was added n-BuLi (2.5M in hexane) (13.0 mL,32.5 mmol) dropwise via syringe over 5 mm. After stirring for 10 mm, the above acid chloride dissolved in THF (20 mL) was added via cannula over 15 mm. The reaction mixture was warmed to 0 C, and was allowed to warm to room temperature as the bath warmed and stirred overnight. To the reaction mixture was added saturated NH4C1, andthen extracted with EtOAc (2x). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography (Teledyne ISCO CombiFlash Rf, 5% to 60% solvent A/B=hexanes/EtOAc, REDISEP Si02 1 20g). Concentration of appropriate fractions provided Intermediate S-1H (7.39 g, 86%) as a colorless oil: ?H NMR (400 MHz, CDC13)o ppm 4.44 (1 H, dt, J=8.31, 3.53 Hz), 4.30 (1 H, t, J=8.69 Hz), 4.23 (1 H, dd, J9.06,3.02 Hz), 2.98-3.08 (2 H, m), 2.32-2.44 (1 H, m, J=13.91, 7.02, 7.02, 4.03 Hz), 2.13-2.25(2 H, m), 1.88-2.00 (2 H, m), 0.93 (3 H, d, J=7.05 Hz), 0.88 (3 H, d, J6.80 Hz).

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; HAN, Wen-Ching; GILL, Patrice; GAVAI, Ashvinikumar, V.; QUESNELLE, Claude, A.; WO2014/47393; (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.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

108149-63-9 (R)-tert-Butyl 4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate 11053464, aoxazolidine compound, is more and more widely used in various fields.

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;,
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,95715-86-9

Example 6. Synthesis of (4S)-4-(morpholin-4-ylcarbonyl)-3-{4-[(trans-3- piperidin-1 -ylcyclobutyl)oxy]phenyl}-1 ,3-oxazolidin-2-one 18.; 6.1. Synthesis of (4S)-3-(tert-butoxycarbonyl)-2,2-dimethyl- 1 ,3-oxazolidine-4- carboxylic acid a61.; Lithium hydroxide (277 mg, 1 1.5 mmol, 1 eq) is added to a solution of methyl 3-tert-butyl 4- methyl (4S)-2,2-dimethyl-1 ,3-oxazolidine-3,4-dicarboxylate a60 (3 g, 1 1.5 mmol, 1 eq) in a tetrahydrof u ran/water mixture (23 ml/11 ml). The mixture is stirred at room temperature for 2 days, acidified to pH 4 with a 1 N aqueous solution of hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases are dried over magnesium sulfate and concentrated under vacuum to afford 2.79 g of (4S)-3-(tert-butoxycarbonyl)- 2,2-dimethyl-1 ,3-oxazolidine-4-carboxylic acid a61 as a yellow oil. Yield: 99 %.LC-MS (MH+): 246.

95715-86-9 Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate 688220, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; UCB PHARMA S.A.; WO2008/128919; (2008); A2;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

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.

To a mixture of 40 (500 mg; 1.14 mmol), 1,1-dimethylethyl (4R)-4-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylate [49](343 mg; 1.48 mmol), and triphenylphosphine (388 mg;1.48 mmol) in THF (10 mL) was added diisopropyl azidodicarboxylate(300 mL; 1.5 mmol) in a dropwise fashion. After stirring atroom temperature overnight, the reaction was concentrated underreduced pressure and the resultant residue was purified by silicagel chromatography eluting with (0-30%). The solid thus obtainedwas washed with MeOH, then dissolved in DCM (5 mL) and treatedwith TFA (5 mL). After 2 h, the reaction was concentrated underreduced pressure and the residue was dissolved in DCM, washedwith aq. NaHCO3, dried (Na2SO4) and concentrated. The solid thatwas obtained was dissolved in a minimal amount of THF andtreated with excess HCl/ether. The resultant precipitatewas filteredto afford the hydrochloride salt of 44 (300 mg, 48%) as a pale yellowsolid. 1H NMR (400 MHz, CDCl3, free base) delta 8.22 (s, 1H), 8.04 (s, 1H),7.97 (s, 1H), 7.71 (d, J 1.96 Hz, 1H), 7.47e7.54 (m, 1H), 7.30e7.39(m, 2H), 6.68 (d, J 8.61 Hz, 1H), 5.79 (s, 2H), 3.83 (d, J 6.26 Hz,2H), 3.42e3.60 (m, 2H), 3.20 (t, J 4.89 Hz, 1H), 2.17 (s, 1H), 2.01 (s,2H). LCMS (APCI) m/z: mass calcd. for C22H18ClF3N4O3S: 510.07,found: 511.2 [(M+H)+].

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

Reference£º
Article; Patch, Raymond J.; Huang, Hui; Patel, Sharmila; Cheung, Wing; Xu, Guozhang; Zhao, Bao-Ping; Beauchamp, Derek A.; Rentzeperis, Dionisios; Geisler, John G.; Askari, Hossein B.; Liu, Jianying; Kasturi, Jyotsna; Towers, Meghan; Gaul, Micheal D.; Player, Mark R.; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 830 – 853;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.131685-53-5,(R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone,as a common compound, the synthetic route is as follows.

Example 15; Step 15A: Compound 15a; (S) -4-Benzyl-3-propionyl-oxazolidin-2-one (46.7 g, 200.0 mmol) was dissolved in THF (870 mL) under inert atmosphere (N2). This was then cooled to-70 C (dry ice/acetone) and treated with sodium hexamethyldisilazide-HMDS (110 mL of a 2. 0M solution in THF, 220.0 mmol) in a dropwise fashion (addition lasted for-45 min. ). The resulting mixture was stirred at-70 C for 1 h. A solution of 4-chlorobenzyl bromide (53.4 g, 260.0 mmol) in THF (160 mL) was then added dropwise over 30 min. The resulting mixture was stirred at-70 C for 6 h and then allowed to warm to room temperature overnight. The reaction was carefully quenched with H20 (100 mL) and the solvent was removed in vacuo. The resulting slurry was suspended in H20 (200 mL) and filtered. The solid was rinsed with EtOAc and air-dried to give 36. 67 g (102.6 mmol, 51%) of 15a. A second crop was obtained from the filtrates after the organic layer was separated, washed with brine, dried (MgS04) and evaporated. The resulting brown solid was suspended in MeOH and filtered to give 17.22 g (48.2 mmol, 24%) of 15a. Only one diastereomer was observed by IH NMR and by single crystal X-ray analysis. IH NMR (Cl3-300 MHz) b 1.18 (d, J = 6.3 Hz, 3H, ) ; 2.66-2. 56 (m, 2 H); 3.16-3. 07 (m, 2H); 4.22-4. 02 (m, 3H); 4. 71- 4.63 (m, 1H) ; 7.08-7. 05 (m, 2H); 7.32-7. 21 (m, 7H)., 131685-53-5

131685-53-5 (R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone 10966403, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2005/42516; (2005); A2;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

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

EXAMPLE III 3-[(6-Nitro-4-chromanylidene)amino]-2-oxazolidinone An 85 g (0.44 mole) portion of 6-nitro-4-chromanone in 460 ml of benzene was treated with 1 ml of HCl (isopropanol) solution, using mechanical stirring, and refluxed until all water was removed via a Dean-Stark trap. The solution was then treated with 46 g (0.46 mole) of 3-amino-2-oxazolidinone and refluxed for 2.6 hr. A 7.9 ml portion of water was collected (theory: 7.9 ml). The reaction mixture was filtered hot, cooled to 10-11 for 3 hrs. and filtered. The orange crystalline solid was washed with 100 ml of benzene, ether and dried, m.p. 168-170. Yield: 107 g (88%). The product was recrystallized from 650 ml of nitromethane (Darco), washed with 100 ml of cold nitromethane, ether and dried, m.p. 170-171, Yield: 84 g (69%). Anal. Calcd. for C12 H11 N3 O5: C, 51.99; H, 4.00; N, 15.16. Found: C, 51.96; H, 4.03; N, 15.14.

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

Reference£º
Patent; Morton-Norwich Products, Inc.; US4093627; (1978); A;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

452339-73-0,452339-73-0, (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

To a solution of (5R)-5- (2, 2-DIMETHYL-4H-1, 3-BENZODIOXIN-6-YL)-1, 3-OXAZOLIDIN-2-ONE (WO 0266422) (2. 00g) in DMF (25ML) under nitrogen was added sodium hydride (60% dispersion in mineral oil, 0. 38g) and the mixture was stirred at room temperature for 15 min. A solution of 4-[(6-BROMOHEXYL) OXY]-1-BUTENE (2. 07G) in DMF (5ml) was added dropwise and the mixture stirred for 3h. The reaction was quenched with water and partitioned between water and EtOAc. The organic phase was washed with brine, dried (MGS04), and evaporated to dryness. The residual oil was purified on a silica SPE bond elut cartridge (50G) using a gradient of 10%-30% EtOAc in cyclohexane (GRADMASTETM). The appropriate fractions were evaporated to give the title compound (2.66g) LCMS RT = 3.47 min.

452339-73-0 (R)-5-(2,2-Dimethyl-4H-benzo[d][1,3]dioxin-6-yl)oxazolidin-2-one 10933894, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXO WELLCOME HOUSE; WO2004/37773; (2004); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

147959-19-1, (S)-tert-Butyl 2,2-dimethyl-4-(2-oxoethyl)oxazolidine-3-carboxylate is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 1 2-FR (1R, 3S)-3-AMINO-4-HYDRY-L- (5-THIAZOLVL)YLLTHIOL-5-CHLORO-3-PYRIDINECARBONITRILE ethanedioate a) (45)-4-R (2R)-2-HVDROXV-2-(2-CHLORO-5-THIAZOLVL) ETHVLL-2*2-DIMETHYL-3- oxazolidinecarboxvlic acid, 1, 1-dimethylethyl ester and (4S)-4-[ (2S)-2-HYDROXY-2- (2- CHLORO-5-THIAZOLYL) ETHYL1-2. 2-dimethyl-3-oxazolidinecarboxylic acid, 1, 1-DIMETHYLETHYL ester n-Butyl lithium (2. 0M in hexanes, 21.6 ml) was added dropwise to a solution of 2-chlorothiazole (5.4 g) in THF (400 ML) at-78 C under a nitrogen atmosphere. After 15 minutes a solution of (4S)-2, 2-dimethyl-4- (2-oxoethyl)-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester (7.0 g) in THF (140 ml) was added dropwise and the reaction mixture was stirred for a further 60 minutes. The cooling was then removed and the mixture was stirred at room temperature for 60 minutes. The reaction mixture was poured into saturated aqueous ammonium chloride and the products extracted with diethyl ether. The combined extracts were washed with brine, dried (magnesium sulfate), filtered and evaporated. Purification by chromatography (silica, 20% ethyl acetate/isohexane as eluent) gave the (4S, 2S) sub-title compound (5.2 g) as a colourless oil. MS APCI +ve m/z 363 [(M+H]). LH NMR 400MHZ (DMSO-D6, 90C) 7.49 (1H, s), 5.69 (1H, d), 4.85 (1H, dd), 3.96-3. 86 (2H, m), 3.84-3. 77 (1H, m), 2.10-1. 99 (IH, m), 1.90 (1H, dt), 1.47 (3H, s), 1.40 (12H, s). Further elution gave the (4S, 2R) sub-title compound (5.1 G, 42%) as a colourless oil. MS APCI +ve m/z 363 ([M+H]). ‘H NMR 400MHZ (DMSO-D6, 90C) 7.49 (1H, s), 5.70 (1H, d), 4.92 (1H, apparent quin.), 4.05-3. 98 (IH, m), 3.91-3. 84 (2H, m), 2.16-2. 07 (1H, m), 1. 84 (1H, ddd), 1.48 (3H, s), 1.41 (12H, s)., 147959-19-1

The synthetic route of 147959-19-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASTRAZENECA AB; WO2004/41794; (2004); 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.2346-26-1,Oxazolidine-2,4-dione,as a common compound, the synthetic route is as follows.

Step 2 3-(2-((3R,4aR,6aS,7R,10bR)-3-(3,4-difluorophenyl)-6a,10b-dimethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethyl)oxazolidine-2,4-dione (4aR,6aS,7R,10bR)-7-(2-bromoethyl)-3-(3,4-difluorophenyl)-6a,10b-dimethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin (150 mg, 0.33 mmol) and potassium carbonate (91 mg, 0.66 mmol) were dissolved in N,N-dimethylformamide (2 mL), added with oxazolidine-2,4-dione (67 mg, 0.66 mmol) and stirred at 80 C. for 1.5 hours. The reaction solution was quenched with water and extracted with dichloromethane (50 mL*3). The organic layer was washed with saturated brine and water, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure and separated on a thin layer chromatography plate to give 3-(2-((3R,4aR,6aS,7R,10bR)-3-(3,4-difluorophenyl)-6a,10b-dimethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethyl)oxazolidine-2,4-dione 215 (70 mg, yield: 44.7%). 1H NMR (400 MHz, CDCl3) 7.36-7.31 (m, 1H), 7.19-7.12 (m, 2H), 5.70 (s, 1H), 4.96 (s, 1H), 4.78 (s, 1H), 4.68 (s, 1H), 4.22 (d, J=11.6 Hz, 1H), 3.68-3.45 (m, 4H), 2.48-1.78 (m, 6H), 1.69 (s, 3H), 1.28-1.25 (m, 3H), 0.79 (s, 3H)., 2346-26-1

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

Reference£º
Patent; Heilongjiang Zhenbaodao Pharmaceutical Co., Ltd.; MEDSHINE DISCOVERY INC.; HE, Haiying; JIANG, Zhigan; XIA, Jianhua; WANG, Jing; HAN, Lixia; LAN, Lihong; ZHOU, Hui; LAI, Kunmin; CHEN, Shuhui; US2018/346438; (2018); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem