Heterocyclic Building Blocks-Oxazolidine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.147959-19-1,(S)-tert-Butyl 2,2-dimethyl-4-(2-oxoethyl)oxazolidine-3-carboxylate,as a common compound, the synthetic route is as follows.

To a cooled, stirred solution of (S)-2,2-Dimethyl-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid tert-butyl ester (4.35 g, CAS 147959-19-1) and (trifluoromethyl)trimethylsilane (2.7 ml) in THF (50 ml) at 0oC. was added dropwise tetrabutylammonium fluoride solution (1.8 ml, 1 M solution in THF). The reaction mixture was allowed to warm to room temperature and then stirred for a further 30 min. The mixture was then diluted with 2 N aq. HCl (50 ml) and stirring was continued for a further 30 min. The mixture was extracted twice with ethyl acetate and the combined organic phases were dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give (S)-2,2-dimethyl-4-((S)-3,3,3-trifluoro-2-hydroxy-propyl)-oxazolidine-3-carboxylic acid tert-butyl ester as a colourless viscous oil (1.6 g, 28%, fractions eluting first) and (S)-2,2-dimethyl-4-((R)-3,3,3-trifluoro-2-hydroxy-propyl)-oxazolidine-3-carboxylic acid tert-butyl ester as a colourless viscous oil (2.0 g, 36%, fractions eluting last)., 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; Galley, Guido; Norcross, Roger; Polara, Alessandra; US2011/112080; (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.2346-26-1,Oxazolidine-2,4-dione,as a common compound, the synthetic route is as follows.

EXAMPLE 7 A mixture of 20.2 g. of 2,4-oxazolidinedione, 6.6 g. of paraformaldehyde and 0.1 g. Ba(OH)2 was melted and heated at 90C. for one hour. The melt was taken into 100 ml. methylene chloride and 18.2 g. phosphorous tribromide added at 0-10C. The mixture was let stand at 25C. overnight, the methylene chloride solution decanted and the solvent removed. The residue was washed with water and recrystallized to give 16.7 g. of 3-bromomethyl-2,4-oxazolidinedione; m.p. 63-64C. An NMR spectrum was consistent with its structure. A mixture of 15.0 g.

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

Reference£º
Patent; Hercules Incorporated; US3962431; (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.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.

875444-08-9, Synthesis of (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-3-((4′-fluoro-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl)d2-methyl)-4-methyl-1,3-oxazolidin-2-one (Compound 176). A solution of 18a (495 mg) in DMF (6 mL) was cooled to -20 C. and a 1M solution of NaHMDS in THF (1.7 mL) was added slowly at <-15 C. Five minutes after the addition was complete, a solution of 17b (480 mg) in DMF (3.5 mL) was added dropwise, keeping the temperature at <-15 C. The reaction was allowed to warm slowly to 16 C. over 2 hr, and stirred for an additional 2 hr. The reaction mixture was diluted with MTBE (200 mL), washed with water (10 mL*2), dilute HCl, then brine, dried (Na2SO4), filtered and the solvent concentrated under reduced pressure to give crude Compound 176. MS m/z=640 (M=H), 662 (M+Na). As the paragraph descriping shows that 875444-08-9 is playing an increasingly important role. Reference£º
Patent; CONCERT PHARMCEUTICALS, INC.; US2008/242711; (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.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: A solution of ferrocenecarboxylic acid (0.93 g, 4.0 mmol), DCC (0.91 g, 4.4 mmol), the required chiral alcohol (4.0 mmol), and DMAP (0.48 g, 4.4mmol) in CH2Cl2 (40 mL) was heated under reflux for 16 h. N,N’-Dicyclohexylurea was filtered off, and the filtrate was washed with water (340 mL). After drying over anhydrous Na2SO4, the solvent was evaporated under reduced pressure, and the ester was isolated by purification by flash chromatography on silica gel. Compound 6c was prepared from 5c (0.93 g) and was isolated (eluent: 88:12 heptane/EtOAc) as a red powder (yield: 76%): mp 70 C; 1H NMR (500 MHz, 340 K, C6D6) delta 1.44 (s, 9H), 1.51 (s, 3H), 1.69 (s, 3H), 3.74 (dd, 1H, J=6.5, 8.8 Hz), 3.89 (d, 1H, J=8.8 Hz), 4.00 (m, 1H), 4.02 (s, 5H), 4.09 (s, 2H), 4.20 (br m, 1H), 4.56 (dd, 1H, J=3.2, 10.4 Hz), 4.81 (d, 2H, J=6.7 Hz); 13C NMR (125 MHz, 340 K, C6D6) delta 23.5, 27.3, 28.6 (3C), 56.7, 63.6, 65.7, 70.1 (5C), 70.7, 70.8, 71.4 (2C), 72.2, 80.0, 94.4, 152.1, 170.7; [alpha]D20 -16 (c 1.0, CH2Cl2). Anal. Calcd for C22H29FeNO5 (443.31): C, 59.60; H, 6.59; N, 3.16. Found: C, 59.30; H, 6.54; N, 3.11. The structure was identified unequivocally by X-ray structure analysis (CCDC 970486) from crystals obtained by slowly evaporating a 2:8 EtOAc/heptane solution., 108149-63-9

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

Reference£º
Article; Dayaker, Gandrath; Sreeshailam, Aare; Ramana, D. Venkata; Chevallier, Floris; Roisnel, Thierry; Komagawa, Shinsuke; Takita, Ryo; Uchiyama, Masanobu; Krishna, Palakodety Radha; Mongin, Florence; Tetrahedron; vol. 70; 12; (2014); p. 2102 – 2117;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

875444-08-9, (4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

875444-08-9, To a solution of (45,,5 ?)-5-[3,5-bis(trifiuorometiiyl)phenyl]-4-methyl-l ,3-oxazolidin-2-one (30.6 g, 98 mmol) in THF (800 mL) was added NaH (60% dispersion in mineral oil) (3.35 g, 84 mmol). After stirring the reaction at room temperature for 10 minutes, 3-bromo-2- (bromomethyl)-6-chloro-4-methylpyridine (16.7 g, 55.8 mmol) was added as a solution in THF (300 mL). The reaction was stirred at room temperature for 16 hours and then quenched with saturated NH4CI (200 mL). The mixture was diluted with EtOAc (1 L). The organic layer was separated, washed with water (500 mL) and brine (500 mL), dried over Na2SC>4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel with 0 to 50% EtO Ac/heptanes afforded (45,5-?)-5-[3.5-bis(trifluoromethyl)phenyl]-3-[(3-bromo-6-chloro-4- methylpyridin-2-yl)methyl3-4-methyl-1,3-oxazolidin-2-one. LCMS = 530.8, 532.8 (M+H)+ 1H NMR (CDCI3, 500 MHz) 5 7.89 (s, 1H), 7.81 (s, 2H), 7.18 (s, 1H), 5.87 (d, J= 8.3 Hz, 1H), 5.04 (d, J = 11.2 Hz, IK), 4.42 (m, 1H), 4.32 (d, J= 17.3 Hz, 1H), 2.43 (s, 3H), 0.80 (d, J= 6.6 Hz, 3H).

The synthetic route of 875444-08-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; LU, Zhijian; CHEN, Yi-Heng; SMITH, Cameron; LI, Hong; THOMPSON, Christopher, F.; SWEIS, Ramzi; SINCLAIR, Peter; KALLASHI, Florida; HUNT, Julianne; ADAMSON, Samantha, E.; DONG, Guizhen; ONDEYKA, Debra, L.; QIAN, Xiaoxia; SUN, Wanying; VACHAL, Petr; ZHAO, Kake; WO2012/58187; (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.152305-23-2,(S)-4-(4-Aminobenzyl)oxazolidin-2-one,as a common compound, the synthetic route is as follows.

Concentrated hydrochloric acid (34.0L, 325.5 mol) was slowly added to a stirred solution of 4-(S)-(4-aminobenzyl)-1,3-oxazolidin-2-one 2 (25.0 kg, 130.2mol) in a mixture of methanol (75.0 L) and water (112.5L) at 5?10 ?C. After stirring for 10 min, a solution of sodium nitrite (11.2 kg, 162.7 mol) in water (75 L) was added slowly to the reaction mixture at 5 to 0?C and the solution was maintained under stirring at the same temperature for 30 min. Meanwhile, in a separate vessel, sodium acetate(42.7 kg, 520.8 mol) was added to a stirred solution of ethyl 2-acetyl-5-(1,3-dioxo-1,3-dihydro-2-isoindolyl) pentanoate (4) (43.3 kg, 136.6 mol) in methanol (437.5 L). After stirring for 1 h at 25?30 ?C the solution was cooled to 0?5 ?C, and the previously prepared diazotized solution was slowly added to this cooled reaction mixture and stirredfor 3 h at room temperature. After the completion of reaction (monitored by thin-layer chromatography, TLC, using ethyl acetate as mobile phase), the reactionmass was extracted three times with dichloromethane (3250 L). The combined dichloromethane layer was washed twice with water (2125 L) and once with brine(125 L). The organic layer was separated and concentrated. The crude residue (containing the hydrazone intermediate) was cyclized to form the indole moiety. Methanol (50 L) and methanolic HCl (15.0percent, 150 mL) were added to the residue. and the solution was refluxed for 6 h. The reaction mass was then cooled to room temperature (25 ?C) and the obtained solid was filtered, washed with methanol (25 L), and dried to furnish the title compound 7. Yield 46.8 kg (78percent); mp 215?220 ?C; 1H NMR: (DMSO-d6, 200 MHz): delta 11.55 (s, 1H), 7.78 (s, 4H), 7.4 (s, 1H), 7.35 (d, 1H, J=8.4 Hz), 7.1 (d, 1H, J=8.4 Hz), 4.25 (q, 2H, J=7.2 Hz), 4.08 (m, 1H), 3.9?3.8 (m, 4H), 3.4?3.3 (m, 2H), 2.9?2.6 (m, 2H), 1.35 (t, 3H, J=7.2 Hz); 13C NMR: (DMSO-d6, 50 MHz): delta 14.2, 23.4, 38.4, 40.9, 51.5, 53.2, 60.4, 68.2, 112.7, 118.9, 119.1, 119.9, 122.9, 123.8, 124.1, 126.7, 127.6, 127.7, 131.6, 134.3, 135.3, 158.7, 161.7, 162.1, 167.7; IR numax cm-1(KBr): 3357 (br), 2940 (br), 1759 (br), 1707, 1544, 1466, 1440, 1396, 1248, 1026 cm-1; MS: m/z 462 (100percent, M1; Et ester).

152305-23-2, 152305-23-2 (S)-4-(4-Aminobenzyl)oxazolidin-2-one 7099156, aoxazolidine compound, is more and more widely used in various.

Reference£º
Article; Vujjini, Satish Kumar; Mothukuri, Vivekananda Reddy; Islam, Aminul; Bandichhor, Rakeshwar; Kagga, Mukkanti; Malakondaiah, Golla China; Synthetic Communications; vol. 43; 24; (2013); p. 3294 – 3306;,
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.

(7S)-3-Chloro-2-chloromethyl-5,6,7,8-tetrahydro-4-(4- methoxyphenyl)-N-[(lR)-l-phenylethyl][l]benzothieno[2,3- b] pyridine-7-carboxamide (1.2 g) obtained in Reference Example 12,2,4-dioxo-1,3-oxazolidine (0.25 g) and potassium carbonate (0.47 g) were added to N,N-dimethylformamide (6 ml), and the mixture was stirred at 80C for 1 hr. The mixture was allowed to cool to room temperature, and acetonitrile (6 ml), 2N HC1 (2 ml) and water (7 ml) were added dropwise. The precipitated crystals were collected by filtration and washed with acetonitrile-water (1: 1, 6 ml) to give the title compound as white crystals (1.27 g, yield 94.3%). ?H-NMR (300 MHz, CDC13) 8; 1.48 (3H, m), 1.67-1.88 (5H, m), 2.41- 2.50 (1H, m) , 2.88-3.17 (2H, m) , 3.88 (3H, s) , 4.91 (2H, s) , 4.99 (2H, s), 5.05-5.17 (1H, m), 5.71-5.73 (1H, m), 6.94-7.34 (9H, m) ., 2346-26-1

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

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/111046; (2005); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

173604-33-6, (R)-4-Benzhydryloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 6Synthesis of Side Chain with Chiral Methyl; Step 1:A 2-L, three-necked, round-bottom flask equipped with a mechanical stirrer and an argon inlet-outlet adapter connected to a bubbler was charged with a solution of (R)-(+)-4-(diphenylmethyl)-2-oxazolidinone (2, 25 g in 200 mL of THF). The solution was cooled to -78 C. under argon. To the solution was added n-butyllithium in hexanes (1.6 M, 64.80 mL) drop wise at -78 C. over a period of 45-60 minutes. The reaction mixture was stirred at -78 C. for 30-45 min. Then, propionyl chloride (20.10 g dissolved in 30-50 mL of dry THF) was added drop wise at -78 C. over 15-30 min. The mixture was stirred at -78 C. for 1-2 h (Note 1). The reaction mixture was quenched with saturated solution of ammonium chloride (15 mL) at -78 C. to -60 C. and then allowed to warm-up to ambient temperature. An additional amount of ammonium chloride (100 mL) was added to the reaction mixture at ambient temperature and the mixture was swirled in separatory funnel. The organic layer was separated from aqueous layer. The aqueous phase was extracted with MTBE (2¡Á100 mL). The combined organic phases were washed with aqueous NaHCO3 (100 mL), brine (100 mL), then dried over anhydrous Na2SO4 followed by filtration. The filtrate was concentrated in vacuo to afford crude solid product (30.38 g, quantitative)., 173604-33-6

The synthetic route of 173604-33-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Lung LLC; US2012/323025; (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.2346-26-1,Oxazolidine-2,4-dione,as a common compound, the synthetic route is as follows.

Reference Example 28 A mixture of 4-[2-(5-methyl-4-phenyl-2-thiazolyl)ethyl]cinnamaldehyde (2.5 g), 2,4-oxazolidinedione (1.14 g), piperidine (0.211 g) and ethanol (50 ml) was refluxed under heating conditions for 4 hours. After the reaction mixture was concentrated, chloroform was added to the residue; the mixture was washed with 2 N HCl and water. The chloroform layer was washed with water, dried (MgSO4) and then concentrated to yield 5-[4-[2-(5-methyl-4-phenyl-2-thiazolyl)ethyl]cinnamylidene]-2,4-oxazolidinedione[mixture of the (E)- and (Z)- configurations](0.81 g, 26%), which was then recrystallized from ethyl acetate to yield light yellow prisms having a melting point of 161-162 C., 2346-26-1

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

Reference£º
Patent; Takeda Chemical Industries, Ltd.; US5614544; (1997); 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.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.

875444-08-9, A solution of (45,,5i?)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-l ,3-oxazoIidin-2-one(614 mg, 1.961 mmol) in THF (20 mL) was cooled to 0 C. NaH (58.8 mg, 2.451 mmol) was added. The mixture was stirred at 0 C for 30 min. The title compound from Step E (462 mg, 1.63 mmol) in THF (30 mL) was added. The mixture was stirred at 0 C and then room temperature for 4 h. Saturated NH4CI (10 mL) was added. The mixture was extracted with ethyl acetate (3 x 10 mL). The combined organic fractions were washed with brine (saturated, 10 mL), dried (Na2S04), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 40S, eluting with EtOAc/hexane (30/70) to give the title compound as a colorless solid. NMR (CDC13} 500 MHz) delta 7.94 (s, 1H), 7.82 (s, 2H), 5.85 (d, J= 8.5 Hz, 1H), 5.00 (d, J- 17.5 Hz, 1H), 4.46 (m, 1H), 4.31 (d, J = 18.0 Hz, 1H), 2.60 (s, 6H), 0.83 (d, J= 7.0 Hz, 3H).

The synthetic route of 875444-08-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; LU, Zhijian; CHEN, Yi-Heng; SMITH, Cameron; LI, Hong; THOMPSON, Christopher, F.; SWEIS, Ramzi; SINCLAIR, Peter; KALLASHI, Florida; HUNT, Julianne; ADAMSON, Samantha, E.; DONG, Guizhen; ONDEYKA, Debra, L.; QIAN, Xiaoxia; SUN, Wanying; VACHAL, Petr; ZHAO, Kake; WO2012/58187; (2012); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem