Heterocyclic Building Blocks-Oxazolidine

152305-23-2, (S)-4-(4-Aminobenzyl)oxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLES; Example 1; Preparation of Zolmitriptan (I)(S)-4-(4-Aminobenzyl)-1,3-oxazolidin-2-one (IX) (100 g) was charged in water (400 ml, 4.0 volumes) and conc. HCl (200 ml, 2.0 volumes) was added at 25-30¡ã C. The solution was cooled to 5 to -10¡ã C. and a solution of sodium nitrite (54 g, 1.5 equivalents) in water (400 ml, 4.0 volumes) was added whilst maintaining the temperature below -5¡ã C. After completion of the addition, the reaction mixture was stirred for 3 hours resulting in the formation of the diazonium chloride (XV) in solution., 152305-23-2

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

Reference£º
Patent; GENERICS [UK] LIMITED; US2011/112157; (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.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.

With key building block 6 in hand, its nitroaldol (Henry) reaction with nitromethane was examined (Table 1). LiAlH418- TBAF19- as well as t-BuOK20-catalyzed Henry reactions led to nitro alcohols 12 and 13 with low diastereoselectivity, reflecting that the existing stereogenic center is too far away from the newly created one to exert appreciable asymmetric induction (Table 1, entries 1-3).21 An obvious way of resolving this problem was the introduction of additional chiral information, i.e. application of a chiral catalyst. In fact double stereodifferentiation using Shibasaki’s well established heterobimetallic (,S)-BINOL catalyst 1422 (5 mol%, THF, -40 C, 3 d) led to 12 with high diastereoselectivity albeit in low yield (Table 1, entry 4).Recently, other highly efficient chiral catalysts for asymmetric Henry reactions have been developed. Thus, Corey23 and Maruoka24 have utilized chiral quaternary ammonium fluorides as catalysts while Trost25 has presented a dinuclear zinc catalyst. Salen-cobalt(II) complexes have been used by Yamada whereas J¡ãrgensen and Evans have introduced bis(oxazoline)-coprhoer(II) complexes. The latter seemed to be the catalysts of choice, at least for aliphatic aldehydes, with respect to attainable yields and degree of stereoselectivity. EPO Table 1. Diastereoselective Henry Reaction of Aldehyde 6 with Nitromethaneyield ratio0 entry catalyst conditions(%)a 12:131 LiAlH4 THF, rt 53 56:442 TBAF THF, rt 33 43:573 r-BuOK t- 72 23:77BuOH/THF,00C4 14 THF, -40 C 45 98:25 {Cu[(+> EtOH, rt 87 92:815]} (OAc)26 (CuK-)- EtOH, rt 85 9:9115]}(OAc)27 {Cu[(+> EtOH, rt 94 97:316]}(OAc)28 (Cu[(-)- EtOH, rt 91 8:9216I)(OAc)2a isolated yield b determined by HPLC analysis of crude reaction mixtures EPO Indeed application of Evans’ bis(oxazoline) copper(II) acetate-based catalysts {Cu[(+)- 15]}(OAc)2 and in particular {Cu[(+)-16]}(OAc)2 (5 mol%, EtOH, rt, 5 d) gave the desired nitro alcohol 12 both with high diastereoselectivity and in high yield (Table 1 , entries 5 and 7). Finally, to obtain selectively diastereomer 13, aldehyde 6 was reacted with nitromethane in the presence of the enantiomeric catalysts {Cu[(-)-15]}(OAc)2 and {Cu[(-)-16]} (OAc)2 respectively. In these cases slightly lower stereoselectivities and yields were observed reflecting a mismatched pairing (Table 1, entries 6 and 8).

147959-19-1, As the paragraph descriping shows that 147959-19-1 is playing an increasingly important role.

Reference£º
Patent; LUDWIG-MAXIMILIANS-UNIVERSITAET MUENCHEN; WO2006/94770; (2006); A2;,
Oxazolidine – Wikipedia
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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

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;,
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.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).

875444-08-9 (4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one 23583229, aoxazolidine compound, is more and more widely used in various fields.

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
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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.

95715-86-9, 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]+.

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; 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

17016-83-0, (S)-4-Isopropyl-2-oxazolidinone is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of 5,5,5-trifluoropentanoic acid (5.04 g, 32.3 mmol) inDCM (50 mL) and DMF (3 drops) was added oxalyl chloride (3.4 mL, 38.8 mmol)dropwise over 5 min and the solution was stirred until all bubbling subsided. Thereaction mixture was concentrated under reduced pressure to give pale yellow oil. To aseparate flask charged with a solution of ( 48)-4-(propan-2-yl)-I ,3-oxazolidin-2-one ( 4.I820 g, 32.4 mmol) in THF (IOO mL) at -78 oc was added n-BuLi (2.5M in hexane, 13.0 mL,32.5 mmol) dropwise via syringe over 5 min. After stirring for IO min, the above acidchloride dissolved in THF (20 mL) was added via cannula over I5 min. The reactionmixture was warmed to 0 C, and was allowed to warm to room temperature as the bathwarmed and stirred overnight. To the reaction mixture was added saturated NH4Cl, and25 then extracted with EtOAc (2x). The combined organics were washed with brine, dried(Na2S04), filtered and concentrated under reduced pressure. The crude material waspurified by flash chromatography (Teledyne ISCO CombiFlash Rf, 5% to 60% solventA/B=hexanes/EtOAc, REDISEP Si02 I20g). Concentration of appropriate fractionsprovided Intermediate S-IB (7.39 g, 86%) as a colorless oil: 1H NMR (400 MHz, CDCh) 8 ppm 4.44 (I H, dt, J=8.3I, 3.53 Hz), 4.30 (I H, t, J=8.69 Hz), 4.23 (I H, dd, J=9.06,3.02 Hz), 2.98-3.08 (2 H, m), 2.32-2.44 (I H, m, J=13.9I, 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, J=6.80 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; GILL, Patrice; QUESNELLE, Claude A.; SAULNIER, Mark G.; GAVAI, Ashvinikumar V.; WO2014/47369; (2014); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

497-25-6,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.

Synthesis of (IR, 2R) and (IS, 2S)-methyl-3-(2-(4-chlorophenyl)-5′-fluoro-2- isopropyl-2′-oxospiro[cyclopropane-l,3′-indoline]-l’-yl)-5-(2-oxooxazolidin-3- yl)benzoate3-bromo-5-((l S,2S)-2-(4-chlorophenyl)-5′-fluoro-2-isopropyl-2′-oxospiro[cyclopropane- 1 , 3 ‘-indoline] – 1 ‘-yl)benzoate, 3 -bromo-5 -(( 1 R,2R)-2-(4-chlorophenyl)-5 ‘-fluoro-2- isopropyl-2′-oxospiro[cyclopropane-l,3′-indoline]-l’-yl)benzoate (0.545 g, 1 mmol), 2- oxazolidone (0.105 g, 1.2 mmol), Cul (20 mg), and K2C03 (0.276 g, 2 mmol) were placed in a Schlenk tube under Argon atmosphere and dissolved in dry acetonitrile. The N, N’- dimethyl- 1,2-ehtanediamine (21 L, 20%equiv) was added into the mixture. The mixture was strirred at 80 C for 14 hours. The solvent was removed in vacuo and the residue was purified by flash column chromatography to give the title compound as white powder (0.40 g, 73%). LC/MS m/e calcd. for C3oH26ClFN205: 548, observed (M+H)+: 549.5

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

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; CHEN, Li; HUANG, Mengwei; FENG, Lichun; HE, Yun; YUN, Hongying; WO2011/69298; (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.80-65-9,3-Aminooxazolidin-2-one,as a common compound, the synthetic route is as follows.,80-65-9

Example 8; Preparation of Compound 35; N-(4-chloro-2-propionylphenyl)-trifluoromethanesulfonamide (2.50 g, 7.9 mmol) and 3-amino-2-oxazolidinone (1.225 g, 11.85 mmol) were mixed in toluene (30 mL). The reaction was heated, with a Dean-Stark apparatus to remove water, at reflux for 3 hrs. The reaction mixture was cooled and evaporated to dryness. The residue was purified on a silica column using 20-100% CH2Cl2/PE, followed by 2% MeOH/DCM as solvent. The product was then recrystallized from DCM/PE to give 2.20 g of white solid. M.p. 115-117 C. 1H n.m.r. (CDCl3) delta 11.82, 1H, b; 7.69, 1H, d, J8.9 Hz; 7.60, 1H, d, J2.2 Hz; 7.42, 1H, dd, J18.9 Hz, J22.3 Hz; 4.54, 2H, t, J7.4 Hz; 3.96, 2H, t, J7.4 Hz; 2.93, 2H, q, J7.6 Hz; 1.13, 3H, t, J7.6 Hz.

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

Reference£º
Patent; Winzenberg, Kevin Norman; Meyer, Adam Gerhard; Yang, Qi; Riches, Andrew Geoffrey; US2007/238700; (2007); 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.497-25-6,Oxazolidin-2-one,as a common compound, the synthetic route is as follows.,497-25-6

A 48 mL pressure vessel containing 2-bromo-4-fluorobenzonitrile (1.00 g, 5.00 mmol), 2-oxazolidone (0.390 g, 4.50 mmol), K2CO3 (0.970 g, 7.0 mmol) and xantphos (0.231 g, 0.40 mmol) in dioxane (10 mL) was degassed with argon for 15 min. Pd2dba3 (0.140 g, 0.15 mmol) was introduced and then the reaction mixture was heated at 70 C. for 18 h. The mixture was cooled, diluted with dioxane, and then filtered through Celite. The resulting mixture was concentrated in vacuo and subjected to column chromatography on silica gel with hexanes:ethyl acetate (1:1) to (3:7) gradient as the eluent to afford the title compound as a white solid (0.460 g, 50% yield): 1H NMR (400 MHz, CDCl3) delta ppm: 7.73 (1H, dd, J=5.8, 8.6 Hz), 7.43 (1H, dd, J=2.5, 9.6 Hz), 7.11 (1H, ddd, J=2.5, 7.5, 8.7Hz), 4.60 (2H, t, J=7.1 Hz), 4.29 (2H, t, J=7.1 HJz); LCMS (+ESI, M+H+) m/z 207.

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

Reference£º
Patent; Bristol-Myers Squibb Company; US2007/111984; (2007); 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.695-53-4,5,5-Dimethyloxazolidine-2,4-dione,as a common compound, the synthetic route is as follows.

695-53-4, To a solution of 7-(3-ethyl-heptyl)-6-(4-formyl-phenoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-2- carbonitrile (720 mg, 1.90 MMOL) in MeOH (30 ml) and THF (30 ml) is added portionwise NaBH4 (100 mg, 2.60 MMOL). The reaction mixture is stirred at rt for 4 h, and the bulk of solvents are removed in vacuo. The residue is diluted with water, and extracted with CH2CI2. The combined organic extracts are washed with brine, and dried over NA2S04, filtered, and concentrated in vacuo. The residue is purified by silica gel column chromatography to give the alcohol 7-(3-ethyl-heptyl)-6-(4-hydroxy-methyl-phenoxymethyl)-7h-pyrrolo[2,3- d]pyrimidine-2-carbonitrile. To a solution of said, alcohol (140 mg, 0.36 MMOL), 5,5-dimethyl-oxazolidinedione (46 mg, 360 MMOL), and Ph3P (105 mg, 0.40 MMOL) in THF (2 mL) is added DEAD (0.25 ml, 0.46 MMOL). The reaction mixture is stirred at rt for overnight. After concentration, the residue is purified by RP-HPLC to give the title compound; Rf 0. 38 (n- Hexane: EtOAc=1: 1) ;H-HMR (400 MHz) 0.92-1. 00 (m, 2H), 1. 18-1. 25 (m, 3H), 1. 30-1. 40 (m, 1H), 1. 58 (s, 6H), 1. 68-1. 78 (m, 7H), 4.35-4. 39 (m, 2H), 4.62 (s, 2H), 5.22 (s, 2H), 6. 71 (s, 1H), 6. 95 (dd, 2H), 7.37 (dd, 2H), 8. 96 (s, 1H).

The synthetic route of 695-53-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/69256; (2004); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem