Heterocyclic Building Blocks-Oxazolidine

108149-60-6, (S)-(-)-3-tert-Butoxycarbonyl-4-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To an ice-cold solution of 5 (3.0 g, 11.6 mmol) in anhydrousTHF (20 mL) was added NaBH4 (4.38 g, 116 mmol) with stirring. After 25 min, MeOH (8 mL) was slowly added. The mixture was warmed to reflux and stirred for 40 min.The resulting suspension was concentrated under reduced pressure and EtOAc (100 mL) was added. The organic layer was washed with water (2 X 50 mL), dried over Na2SO4, filtered and concentrated to give 6 as colorless oil (2.67 g,85% yield): [alpha]D21 +21.7 (c 1.2, CHCl3), lit: []D20 +23.8 (c1.2, CHCl3) [17]; IR v 3436, 2979, 2937, 2880, 1671, 1477,1456, 1388, 1365 cm-1; 1H NMR (200 MHz, CDCl3) (ppm): 3.92-3.47 (m, 6H, CH2OH, CH2O, OH, CHN), 1.47,1.41 (s, 15H, C(CH3)2, C(CH3)3); 13C NMR (50 MHz, CDCl3) (ppm): 153.68 (C=O), 93.83 (C), 80.92 (C(CH3)3),65.10, 64.24 (CH2O, CH2OH), 59.21 (CHN), 28.25(C(CH3)3), 27.04, 24.37 (CH3)., 108149-60-6

The synthetic route of 108149-60-6 has been constantly updated, and we look forward to future research findings.

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

90319-52-1, (R)-4-Phenyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: n-Butyllithium (1.15mL, 1.0equiv, 2.3M in hexanes) was added to a cooled until ?75¡ãC solution of the corresponding oxazolidinone (2.6mmol) in anhydrous THF (12mL), then the resulting solution was warmed to ?30¡ãC and stirred for 20min. At the same temperature, a solution of cinnamoyl chloride (1.0equiv) in anhydrous THF (7mL) was added dropwise and then allowed to rise to at room temperature and left overnight with continuous stirring. After work-up with 10percent NH4Cl (15mL), the organic layer was separated and the aqueous layer was extracted with ethyl acetate (2¡Á25ml). The combined organic phase was dried over Na2SO4, filtered and evaporated under reduced pressure. The crude products were purified by chromatography or crystallized from appropriate solvents. 4.3.1 (R)-4-Phenyl-3-[(E)-(3-phenylacryloyl)]-oxazolidin-2-one 2a. White crystals (0.28g, 62percent yield) after crystallization (Et2O/EtOAc, 1:1); mp 169?170¡ãC. 1H NMR (200MHz, CDCl3) delta 4.32 (dd, J=3.8, 8.8Hz, 1H, NCHCH2), 4.74 (t, J=8.8Hz, 1H, NCHCH2), 5.56 (dd, J=3.8, 8.8Hz, 1H, NCHCH2), 7.28?7.48 (m, 8H, aromH), 7.52?7.66 (m, 2H, aromH), 7.78 (d, J=15.7Hz, 1H, CH=CH?CO), 7.95 (d, J=15.7Hz, 1H, CH=CH?CO). 13C NMR (75MHz, CDCl3) delta 58.0, 70.1, 117.0, 126.1, 128.7, 128.8, 129.0, 129.3, 130.8, 134.6, 139.2, 146.8, 153.9, 164.9, 90319-52-1

90319-52-1 (R)-4-Phenyloxazolidin-2-one 730425, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Article; Leitis, Zigm?rs; L?sis, Viesturs; Tetrahedron Asymmetry; vol. 27; 17-18; (2016); p. 843 – 851;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.108149-60-6,(S)-(-)-3-tert-Butoxycarbonyl-4-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine,as a common compound, the synthetic route is as follows.

A solution of (i?)-3-tert-butyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate (5 g, 19.3 mmol) in anhydrous diethyl ether was chilled in an ice bath and 1 M LiAlH4 in diethyl ether (38 mL, 38.6 mmol) was added dropwise under an N2 atmosphere. The reaction was allowed to warm to room temperature with stirring overnight. The reaction was quenched by slowly adding saturated aqueous Na2SO4 (5 mL). The slurry was filtered through a pad of Celite.The Celite pad was rinsed with EtOAc and the solution was dried in vacuo to yield (S)-tert-buty4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate (2.77 g, 12 mmol) as a clear oil.[M+H] calc’d for CnH2INO4, 232; found, 232., 108149-60-6

The synthetic route of 108149-60-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2009/97578; (2009); 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.99395-88-7,(S)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

Add 10 ml of dichloromethane, 500 ml of triethylamine (3.6 mol), and phenyloxazolidinone 163 g to a 5-liter four-necked bottle.(1 mol), propionic acid 80 g (1.1 mol), 300 g (1 mol)2-chloropyridine methyl p-toluenesulfonate salt 1000 ml of dichloromethaneThe solution was added and stirred at 25 C for 5 hours. TLC showed the reaction was complete, and the mixture was extracted with water and washed with water and saturated brine.The organic phase was dried over anhydrous sodium sulfate, concentrated, and then recrystallised to give product 200 g, yield: 91.3%, HPLC purity >99%., 99395-88-7

As the paragraph descriping shows that 99395-88-7 is playing an increasingly important role.

Reference£º
Patent; Shanghai Lark Pharmaceutical Technology Co., Ltd.; Shen Xin; Yang Jidong; Hu Xiaochuan; Li Feng; (6 pag.)CN109020914; (2018); A;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

99395-88-7, (S)-4-Phenyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 4 PREPARATION OF 1-[(5-METHOXY-1,5-DIOXOPENTA)-YL1-4-(S)-PHENYL OXAZOLIDIN-2-ONE (FORMULA III) 300 g of monomethyl glutarate was taken into a four neck round bottom flask containing 1500 ml of dichloromethane under stirring. 684 ml of triethyl amine was added at 20 C. followed by the addition of 306 ml of pivaloyl chloride. The reaction mixture was stirred at room temperature for 3 hours. 267 g of (S)-4-Phenyl-2-oxazolidinone and 17 g of dimethyl aminopyrimidine was added and heated to 45 C. The reaction mass was maintained at 42 to 45 C. for 7 hours. Reaction completion was confirmed by thin layer chromatography. The reaction mass was cooled to room temperature and 1500 ml of water was added to it. The aqueous layer was separated and extracted with 750 ml of dichloromethane in two equal lots. Total organic layer was washed with 750 ml of water in two equal lots. The organic layer was evaporated under vacuum at 63 C. to get an oily compound. 1200 ml of n-heptane was charged to this oily compound and stirred for 60 minutes. Filtered the separated solid and washed with 600 ml of n-heptane. The compound was dried at 30 C. for 8 hours to get 449 g of the title compound as a crystalline solid. (Yield 75%) Purity by HPLC: 93.48%., 99395-88-7

The synthetic route of 99395-88-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Uppala, Venkata Bhaskara Rao; Vaddadi, Pattabhi Ramayya; Sunkara, Vishnu Vardhan; Cheemalapati, Venkata Annapurna Sasikala; Padaga, Kanaka Seshu Kumar; US2007/49748; (2007); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

90319-52-1, (R)-4-Phenyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 24 3-[(3R)-1-oxo-3-[3-(phenylmethoxy)phenyl]pentyl]-4R-phenyl-2-Oxazolidinone The 4R-phenyl-2-oxazolidinone (3.5g, 21.4mmol) was placed in a three-necked flask, after it was purged with nitrogen, tetrahydrofuran was added and it was cooled to -78¡ãC, then n-butyl lithium (1.6M, 13.8ml, 22mmol) was added dropwise, and the reaction was carried out for 30 minutes. After that, a solution of (R)-3-(3-(benzyloxy) phenyl) pentanoyl chloride (7.1g, 23.6mmol) in tetrahydrofuran was added dropwise, the reaction was continued for 30 minutes, then it was slowly raised to 0¡ãC, the reaction was continued for 2 hours, and then quenched with saturated ammonium chloride solution. The reaction solution was then concentrated to remove tetrahydrofuran and extracted with ethyl acetate 3 times, then the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated, and recrystallized with petroleum ether and ethyl acetate to give a white solid 8.6g, yield: 85percent. 1HNMR(CDCl3): delta 7.3-7.5 (8H, m), 7.1-7.2(3H, m), 6.7-6.9(3H, m), 5.2(1H, dd, J=3.7,8.6), 5.1(2H, s), 4.5(1H, t, J=8.9,17.1), 4.2(1H, dd, J=3.5,8.6), 3.5(1H, dd, J=8.9,16.4), 3.2(1H, d, J=5.6), 3.1(1H, m), 1.5-1.7(2H, m), 0.9(3H, t, J=7.3,14.7). ESI-MS: 430.5(M+H)., 90319-52-1

The synthetic route of 90319-52-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Shanghai Institute Materia Medica, Chinese Academy Of Sciences; Topharman Shanghai Co., Ltd.; ZHANG, Qiang; ZHANG, Rongxia; TIAN, Guanghui; LI, Jianfeng; ZHU, Fuqiang; JIANG, Xiangrui; SHEN, Jingshan; EP2671878; (2013); 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,147959-19-1

To a stirred solution of (S)-2,2-dimethyl-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid tert-butyl ester (15.5 g; CAS 147959-19-1) in dry diethyl ether (100 ml) under an argon atmosphere at room temperature was added dropwise a solution of ethylmagnesium bromide in diethyl ether (42.6 ml, 3 M solution) and stirring continued for 1 hour. The reaction mixture was then quenched by careful addition of water (10 ml) and the mixture was then filtered through decalite. The filtrate was washed sequentially with water and with saturated brine and then the organic phase was separated, dried over sodium sulphate, filtered and concentrated in vacuo. The reside was purified by column chromatography (SiO2; gradient: heptane/EtOAc 100:0?50:50) to give (S)-4-((R)-2-hydroxy-butyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (7.30 g) from fractions eluting first and (S)-4-((S)-2-hydroxy-butyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (6.44 g) from fractions eluting later, both compounds as colourless oils. (S)-4-((R)-2-Hydroxy-butyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester: 1H NMR delta (CDCl3, 300 MHz): 4.52 (1H, br. D, J=3.3 Hz), 4.23 (1H, m), 4.00 (1H, dd, J=8.7 & 5.4 Hz), 3.66 (1H, d, J=8.7 Hz), 3.40 (1H, m), 1.79 (1H, td, J=11.4 & 2.1 Hz), 1.60-1.44 (16H, m), 0.95 (3H, t, J=7.5 Hz). (S)-4-((S)-2-Hydroxy-butyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester: 1H NMR delta (CDCl3, 300 MHz): 4.12 (1H, m), 3.98 (1H, dd, J=9.0 & 5.7 Hz), 3.82 (1H, m), 3.55 (1H, m), 2.88 (1H, br. s), 1.79 (1H, m), 1.70-1.40 (16H, m), 0.95 (3H, t, J=7.5 Hz).

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

Reference£º
Patent; Galley, Guido; Goergler, Annick; Groebke Zbinden, Katrin; Norcross, Roger; US2010/29589; (2010); 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.139009-66-8,(S)-N-Boc-2,2-dimethyloxazolidine-4-carboxylic Acid,as a common compound, the synthetic route is as follows.

Step 3: Preparation of (S)-tert-butyl-4- (3 -(4-chlorobenzoyl)-4,5-dimethylthiophen-2- ylcarbamoyl)-2 ,2-dimethyloxazolidine-3 -carboxylate (Intermediate 44) To a solution of (S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid (Intermediate 4, 0.886 g, 3.61 mmol) in DCM (9 mL) was added Nmethylmorpholine (NMM) (0.397 mL, 3.61 mmol) followed by isobutyl chioroformate (0.474 mL, 3.61 mmol) at 0 C. The mixture was stirred for 30 mm at room temperature. After addition of (2-amino-4,5-dimethylthiophen-3 -yl)(4- chlorophenyl)methanone (Intermediate 43, 0.800 g, 3.01 mmol) to the mixture, thereaction mixture was stirred for 2 days at room temperature. The reaction mixture was diluted with DCM, washed with 2 N aq. HC1, saturated aq. NaHCO3 and water, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on Si02 (Hex:EtOAc = 5:1 to 3:1 to 1:1) to obtain the title compound (1.80 g, 88%) as a viscous yellow oiL ?H-NMR (400 MHz, CDC13): (two sets from rotamers) 11.4 (brs, ill), 7.53 (d, J= 8.0 Hz, 2H), 7.41 (d, J= 8.4 Hz, 2H), 4.65-4.13 (m, 3H), 2.26 (s, 3H), 1.84 and 1.79 (s and s, 3H), 1.68 (s, 3H), 1.57 and 1.56 (s and s, 4H), 1.47 (s, 3H), 1.29- 1.24 (rn, 5H)., 139009-66-8

139009-66-8 (S)-N-Boc-2,2-dimethyloxazolidine-4-carboxylic Acid 6932187, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; KAINOS MEDICINE, INC.; OH, Su-Sung; CHOI, Minjeong; WO2015/156601; (2015); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

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, To a solution of hex-5-enoic acid (11.24 g, 87.0 mmol), (4R)-4-isopropyl-1, 3-oxazolidin- 2-one (12.91 g, 113. 1 mmol) and DMAP (1. 06 g, 8.70 mmol) in CH2CI2, was added DCC (23.33 g, 113. 1 mmol) at 0 C and the mixture was stirred at 0 C for 15 min. Then the mixture was stirred at room temperature overnight and was filtered through a pad of celite and the filtrate was washed with sat. NaHCO3aq. The organic layer was dried over Na2SO4, filtered and evaporated. The crude product was purified by silica gel column chromatography (hexane-AcOEt 20: 1-10: 1) to give the titled compound (16.60 g, 73.7 mmol). 1H NMR (CDCI3) 6 : 5.90-5. 70 (m, 1H), 5.10-4. 95 (m, 2H), 4.50-4. 42 (m, 1H), 4.35-4. 15 (m, 2H), 3.10-2. 80 (m, 2H), 2.46-2. 30 (m, 1H), 2.20-2. 08 (m, 2H), 1.90-1. 68 (m, 2H), 0.92 (d, J = 7.1 Hz, 3H), 0.88 (d, J= 6.9 Hz, 3H) ppm

The synthetic route of 95530-58-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PFIZER JAPAN, INC.; PFIZER INC.; WO2005/80317; (2005); 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

875444-08-9, Step 6: Synthesis of (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-3-((5′-ethyl-4′-fluoro-2′-methoxy-4- (trifluoromethyl)biphenyl-2-yl)methyl)-4-methyloxazolidin-2-one (desmethylanacetrapib, DMAP); The chiral intermediate (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one (compound of formula XV; cf. also compound 11 in Scheme 3) (280 mg) prepared by procedure of WO 2007/005572 is dissolved in DMF (30 mL) and cooled to -15C. 2 M NaHMDS (3.90 mL, 1.05 eq) was then added over 1 h, followed by addition of the biaryl chloride EBFCI (270 mg) in DMF (5 mL), maintaining the internal temperature below -10 C. The mixture was warmed to +12 C and was aged until complete conversion took place. Then 5M HCI (3.5 mL) was added, followed by 20 mL of 10% IPAC/Heptanes and 40 mL of water, keeping the temperature between 10C and 20C throughout. The layers were cut and the organic layer was washed twice with 20 mL of 1/1DMF/water followed by two 15 mL water washes. The organic layer was then removed under reduced pressure and the resulting residue was purified by flash chromatography (EtOAc/hexanes) to remove the excess oxazolidinone (compound of formula XV). The pure (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-3-((5′-ethyl-4′- fluoro-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl)methyl)-4-methyloxazolidin-2-one (DMAP, compound of formula XI I”) was obtained as a colorless oil (388 mg, 80%).

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; LEK PHARMACEUTICALS D.D.; HUMLJAN, Jan; MARAS, Nenad; WO2012/85133; (2012); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem