Heterocyclic Building Blocks-Oxazolidine

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.

REFERENCE EXAMPLE 19 (S)4-(1-Methylethyl)-3-(1-oxo-3-phenylpropyl)-2-oxazolidinone To a solution of 2.5 g of (4S)4-isopropyl-2-oxazolidinone in 60 ml of dry tetrahydrofuran under argon, cooled to -78 C. was added 8 ml n-butyllithium (2.5M in hexane). The suspension was allowed to warm slowly to 0 C. and then cooled to -78 C. (total time 50 minutes). To the well stirred suspension was added dropwise 3.3 ml of 3-phenylpropionyl chloride. The resulting solution was stirred at -78 C. for 2 hours and at 0 C. for 0.5 hour. To the solution was added 20 ml of saturated sodium bicarbonate and mixture concentrated under reduced pressure. The suspension was diluted with 20 ml of water and extracted with 150 ml of ethyl acetate. The extract was washed with brine, dried (Na2 SO4) and the solvent removed to give 5.67 g of colorless oil. This oil crystallized on standing and the crystals were triturated with hexane to give 5.0 g of crystals; [alpha]D26 +71+-1 (c, 1.182, CHCl3).

The synthetic route of 17016-83-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; American Cyanamid Company; US5104869; (1992); A;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

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.

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
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

To a stirred suspension of sodium hydride (60% dispersion in mineral oil; 1.3 g; 0.0325 mol) in THF (60mL) at 0 C under N2 was added dropwise a solution of (4S,5ft)-5-[3,5-bis(trifluoromethyl)phenyi]-4-methyl-l,3-oxazolidin-2-one (Example 17) (4.077 g; 0.013 mol) in THF (50 mL). Gas evolution wasobserved. The resultant mixture stirred at 0 C for 30 min prior to addition of a solution of 2-(bromomethyl)-l-iodo-4-(trifluoromethyl)benzene (4.754 g; 0.013 mol) in THF (20 mL). The reactionwas allowed to warm to room temperature and stirred for 14 h. The reaction was carefully quenchedwith H2O (15 mL) and partitioned between EtOAc (250 mL) and H2O (75 mL). The aqueous layer wasextracted with EtOAc (3 x 100 mL). Combined organic layers were washed with brine (100 mL), dried(MgSO4), filtered and concentrated in vacua. The residue was purified by flash chromatography (0-20%EtOAc/hexanes gradient) to afford 6.4 g (82.5%) of (4S,5fl)-5-[3,5-bis(trifluoromemyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]-4-methyl-l,3-oxazolidin-2-one as a white solid. LCMS = 598.1 (M+l)+.*H NMR (CDC13, 500 MHz): 5 8.03 (d, J = 8.2 Hz, 1 H), 7.90 (s, 1 H), 7.79 (s, 2 H), 7.58 (s, 1H), 7.30(dd, J = 8.2 Hz, J = 2.0 Hz, 1 H), 5.76 (d, J = 8 Hz, 1 H), 4.88 (d, J = 15.8 Hz, 1 H), 4.37 (d, J = 15.8 Hz,1 H), 4.09-4.02 (m, 1 H), 0.8 (d, J = 6.6 Hz, 3 H).

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.

Reference£º
Patent; MERCK & CO., INC.; WO2006/14357; (2006); 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).

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
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.

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
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

EXAMPLE 24 – Synthesis of [(5)-4-(3-cyano-benzenesulfonyl)-2-(2,4-dioxo-oxazolidin-3- ylmethyl)-3,4-dihydro-2H-benzo[l,4]oxazin-6-yl]-carbamic acid tert-butyl ester (24) [0282] To a solution of triphenylphosphine (1.2 g, 4.7 mmol) in tetrahydrofuran (7.5 mL) at 0 C was added diisopropylazodicarboxylate (0.9 mL, 4.7 mmol). After fifteen minutes, [(i?)-4-(3-cyano-benzenesulfonyl)-2-hydroxymethyl-3,4-dihydro-2H-benzo[l,4]oxazin-6-yl]- carbamic acid tert-butyl ester (1.4 g, 3.1 mmol) and 2,4-oxazolidinedione (0.3 g, 3.1 mmol) in tetrahydrofuran (7.5 mL) was added dropwise. After the addition was complete the mixture was allowed to warm to room temperature. The mixture was stirred an additional three hours, and partitioned between dichloromethane and 1 N HCl. The organic layer was dried (Na2SC”4) and concentrated to afford [(5)-4-(3-cyano-benzenesulfonyl)-2-(2,4-dioxo-oxazolidin-3-ylmethyl)- 3,4-dihydro-2H-benzo[l,4]oxazin-6-yl]-carbamic acid tert-butyl ester. LCMS ESI calculated for C24H25N408S (M+H)+: 529, Found: 529.

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

Reference£º
Patent; MERCK SHARP & DOHME CORP.; LYCERA CORPORATION; AICHER, Thomas D.; VAN HUIS, Chad A.; THOMAS, William D.; MACLEAN, John K.; ANDRESEN, Brian M.; BARR, Kenneth J.; BIENSTOCK, Corey E.; ANTHONY, Neville J.; DANIELS, Matthew; LIU, Kun; LIU, Yuan; WHITE, Catherine M.; LAPOINTE, Blair T.; SCIAMMETTA, Nunzio; SIMOV, Vladimir; WO2015/95795; (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.2346-26-1,Oxazolidine-2,4-dione,as a common compound, the synthetic route is as follows.

PREPARATION A 3-Triphenylmethyl-1,3-oxazolidine-2,4-dione To a solution of 1,3-oxazolidine-2,4-dione (60.7 g, 0.600 mol) and triethylamine (60.7 g, 0.600 mol) in methylene chloride (500 mL) was added triphenylmethyl chloride (167.3 g, 0.600 mol). After 30 minutes, the thick white solid was collected by vacuum filtration, washed with water (2 L) and dried in a vacuum desicator to give the title compound (201.4 g, 96%). A portion was recrystallized from chloroform to give white plates: mp 216-218 C.

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

Reference£º
Patent; Pfizer Inc.; US5037842; (1991); A;,
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

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).

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

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

Synthesis of (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-3-((4′-fluoro-5′-(1,1,1,2,3,3,3-d7)isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl)methyl)-4-methyl-1,3-oxazolidin-2-one (Compound 164). A solution of (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyl-1,3-oxazolidin-2-one (18a) [prepared by methods described in WO2007/005572] (112 mg) in DMF (2 mL) was cooled to -20 C. and 1M NaHMDS in THF (0.4 mL) was added slowly, maintaining the reaction temperature at <-15 C. After 5 min, a solution of 17a (110 mg) in DMF (0.5 mL) was added dropwise at <-15 C. The reaction mixture was allowed to warm slowly to 15-16 C. and stirred for 2 hr. The mixture was diluted with MTBE (50 mL) and the solution washed with water (10 mL*2), dilute HCl solution, brine, dried (Na2SO4), filtered and the solvent removed under reduced pressure. The crude product was purified by chromatography on silica gel to give 10 mg of Compound 164. MS m/z=645 (M+H), 667 (M+Na). 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. 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.160695-26-1,(R)-4-Phenyl-3-propionyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

Example-21: Preparation of (R)-3-((S)-2-methylpent-4-enoyl)-4-phenyloxazolidin-2-one (Formula B-II) A solution of (R)-4-phenyl-3-propionyloxazolidin-2-one compound of formula B-I (100 gm) in tetrahydrofuran (500 ml) was slowly added to a pre-cooled mixture of sodium bis(trimethylsilyl)amide (240 ml) in tetrahydrofuran (500 ml) at -70C to -75C under N2 atmosphere and stirred for 1 hr at the same temperature. Allyl bromide (60 ml) was slowly added to the reaction mixture at -70C to -75C and stirred for 1 hr at the same temperature. Raised the temperature of the reaction mixture to 0-5C and stirred for 1 hr at the same temperature. Aqueous ammonium chloride solution followed by methyl tert.butyl ether were added to the reaction mixture at 0-5C. Raised the temperature of the reaction mixture to 25- 30C and stirred for 15 min at the same temperature. Both the organic and aqueous layers were separated and washed the organic layer with aqueous sodium chloride solution. Distilled off the solvent completely from the organic layer under reduced pressure and co- distilled with isopropyl alcohol. 300 ml of isopropyl alcohol was added to the obtained compound. Heated the reaction mixture to 60-65 C and stirred for 15 min at the same temperature. Cooled the reaction mixture to 0-5C. Petroleum ether (300 ml) was slowly added to the precipitated solid at 0-5 C and stirred for 60 min at the same temperature. Filtered the solid, washed with petroleum ether and dried to get the title compound. Yield: 65.0 gm; M.R: 68-70C.

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

Reference£º
Patent; MSN LABORATORIES PRIVATE LIMITED; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; VENKAT REDDY, Ghojala; WO2015/87351; (2015); A2;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem