Heterocyclic Building Blocks-Oxazolidine

139009-66-8, (S)-N-Boc-2,2-dimethyloxazolidine-4-carboxylic Acid is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Before being used, the reactor was freed with DCM, dried under vacuum and purged by flushing with nitrogen for 15 to 30 min, the Erlenmeyer flask is rinsed with amylene-stabilized DCM and then dried under nitrogen. The reactor was charged with 95 ml of DCM and 34.0 g of boc-L-serine acetonide, cooled to 4-10 C. and 14.3 g of N-methylmorpholine were added using a dropping funnel while maintaining the temperature at 4-10 C. The dropping funnel was rinsed with 2.5 ml of DCM. 17.1 g of pivaloyl chloride were added using a dropping funnel while maintaining the temperature at 4-10 C. and the dropping funnel was rinsed with 2.5 ml of DCM. The mixture is kept stirred at 4-10 C. for 2 h.A solution of aminobal (20.0 g) in DCM (95 ml) was prepared with stirring and this solution was added to the reactor while maintaining the temperature at 4-10 C. The mixture was subsequently heated to 20 C. over 1 h and was kept stirred at 20 C. for a minimum of 16 h. 100 ml of demineralized water was added to the reactor at 20-25 C. and the mixture was left stirring for 20 min and separated by settling. The lower organic phase comprising the product and the upper phase (predominantly aqueous) were withdrawn. The organic phase comprising the product was again charged to the reactor. 140 ml of a 1.0 N aqueous sodium hydroxide solution were added. The mixture was kept stirred at 20-25 C. for approximately 20 min and then allowed to separate by settling. The lower organic phase comprising the product was withdrawn. The organic phase comprising the product was again charged to the reactor. 100 ml of demineralized water were added. The mixture was kept stirred at 20-25 C. for approximately 20 min and then allowed to separate by settling. The lower organic phase comprising the product was withdrawn. The organic phase comprising the product was again charged to the reactor. 100 ml of isopropanol was added.Distillation was carried out (35+/-5 C. in the jacket) under a residual pressure of approximately 30 mbar until a residual volume of 100 ml was present in the reactor. The temperature was adjusted to 20 C. and the mixture was left stirring at 20 C. for 3 h. The reactor was rinsed and the cake was washed twice with a total volume of 40 ml of isopropanol. The product was dried at 40 C. under a vacuum of 30 mbar. Yield of isolated product: 60%., 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; C/O SANOFI; US2012/302759; (2012); 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. The solution was stirred until all bubbling subsided. The reaction5 mixture was concentrated under reduced pressure to give a pale yellow oil. To a separateflask charged with a solution of ( 48)-4-(propan-2-yl)-1 ,3-oxazolidin-2-one ( 4.18 g, 32.4mmol) in THF (100 mL) at -78 oc was added n-BuLi (13.0 mL, 32.5 mmol, 2.5M inhexane) dropwise via syringe over 5 min. After stirring for 1 0 min, the above acidchloride dissolved in THF (20 mL) was added via cannula over 15 min. The reaction10 mixture 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, andthen extracted with EtOAc (2x). The combined organics were washed with brine, dried(Na2S04), filtered and concentrated under reduced pressure. The crude material waspurified by silica gel chromatography (hexanes/EtOAc) to provide Intermediate S IA15 (7.39 g, 86%) as a colorless oil: 1H NMR (400 MHz, CDCh) 8 4.44 (1 H, dt, J=8.31, 3.53Hz), 4.30 (1 H, t, J=8.69 Hz), 4.23 (1 H, dd, J=9.06, 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, J=6.80 Hz).

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; GAVAI, Ashvinikumar V.; ZHAO, Yufen; O’MALLEY, Daniel; QUESNELLE, Claude A.; FINK, Brian E.; NORRIS, Derek J.; HAN, Wen-Ching; DELUCCA, George V.; WO2014/47374; (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.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, To a solution of (4S,5R>5-[3,5-bis(trifluoromethyl) phenyl]-4-methyl-l,3-oxazolidin-2-one (0.050 g,0.16 mmol) in THF (1 ml) at 0C, NaH (7.6 mg, 0.19 mmol, 60%) was added. The mixture was stirred at0C for 30 min. The title compound from Step A (0.059 g, 0.21 mmol) was added. The whole mixturewas stirred at 0C for 1 h and warmed to room temperature for 4 h. The reaction was quenched withsaturated ammonium chloride. The organic was extracted with ethyl acetate (3 x 15 ml). The combinedethyl acetate layers were washed with brine and dried over sodium sulfate. The title compound wasobtained after preparative TLC purification using EtOAc:hexane = 2:8 as the elute. IH NMR (CDC13,500 MHz) 5 7.92 (s, IH), 7.82 (s, 2H), 7.55 (d, J = 8.5 Hz, IH), 7.43 (d, J = 2.5 Hz, IH), 7.23 (dd, J =8.5, 2.5 Hz, IH), 5.77 (d, / = 8.0 Hz, 1H),4.86 (d, J = 16.0 Hz, IH), 4.36 (d, J = 16.0 Hz, IH), 4.11 (m,ffl),0.82(d,J = 6.5Hz, 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 & 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.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, Take 100ml round mouth flask, add intermediate V and methylene chloride, cool to below 5 , stirring slowly dropping thionyl chloride.The resulting reaction mixture was incubated at 15-20 & lt; 0 & gt; C for 2-3 hours and the TLC monitoring reaction was complete.The mixture was stirred with water for 10 minutes, and the layers were allowed to stand apart. The aqueous layer was removed and compound VI was added to a 100 ml round bottom flask followed by tetrabutylammonium iodide, K2CO3, And the mixture was stirred at 60 C for 16-18 hours. TLC was used to monitor the reaction. After completion of the reaction, n-heptane and water were added under heat.The aqueous layer was discarded and the organic layer was washed with water (3 times) and concentrated to give a yellow liquid, which was added with ethanol: water (1: 20 by volume) and allowed to stand to give a white powder. The final product Compound).Yield 72%.

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; Hunan Qianjin Xiang River Pharmaceutical Co., Ltd.; Jin Bingde; Yao Liangyuan; Wang Qiongyao; Tian Yao; Sima Yingyu; (14 pag.)CN106032362; (2016); 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.2346-26-1,Oxazolidine-2,4-dione,as a common compound, the synthetic route is as follows.,2346-26-1

3.3. 3-(2-{1-[3-(Trifluoromethyl)phenyl]-4-piperidyl}ethyl)-1,3-oxazolidine-2,4-dione A solution of 2.3 g (6.545 mmol) of 2-{1-[3-(trifluoromethyl)phenyl]-4-piperidyl}ethyl methanesulfonate, prepared in step 3.2, 0.694 g (6.87 mmol) of 1,3-oxazolidine-2,4-dione (J. Med. Chem., 1991, 34, 1538-1544) and 1.5 g (13.09 mmol) of 1,1,3,3-tetramethylguanidine in 30 ml of tetrahydrofuran is refluxed for 12 hours under an inert atmosphere. The mixture is concentrated under reduced pressure. The residue is taken up in dichloromethane and water, the aqueous phase is separated out and extracted twice with dichloromethane, and the combined organic phases are washed with saturated aqueous sodium chloride solution and dried over sodium sulfate. After evaporating off the solvent, the residue obtained is purified by chromatography on silica gel, eluding with a 20/80 and then 40/60 mixture of ethyl acetate and cyclohexane. 1.61 g of pure product are obtained in the form of an oil.

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

Reference£º
Patent; Sanofi-Aventis; US2006/89344; (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.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, 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) (28.0 g) prepared by the procedure of WO 2007/005572 is dissolved in DMF (300 mL) and cooled to -15C. 2 M NaHMDS (39.2 mL, 1.05 eq) was then added over 1 h, followed by addition of the blaryl chloride 7 (Scheme 3) (28.0 g) in DMF (50 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 HCl (35 mL) was added, followed by 160 mL of 10% IPAC/Heptanes and 340 mL of water, keeping the temperature between 10C and 20C throughout. The layers were cut and the organic layer was washed twice with 150 mL of 1/1 DMF/water followed by two 140 mL water washes. The organic layer was then removed under reduced pressure and the resulting residue was purified by flash chromatography (EtOAclhexanes) to remove the excess oxazolidinone 11 (Scheme 3). The obtained colorless oil was then dissolved in refluxing heptanes (200 mL) and the solution was slowly cooled to -20 C. The resulting slurry was then stirred at -20 C for 2 hours and filtered. The filter cake was washed with cold heptanes and was then dried, yielding 44.0 g (88%) of the desired product of compound of formula XV” (anacetrapib) as an amorphous material. An impurity of compound of formula XVII” (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-3-((5′-ethyl-4′-fluoro-2′-methoxy-4-(triftuoromethyl) biphenyl-2-yl)methyl-4-methyloxazolidin-2-one (DMAP) is present in the thus obtained anacetrapib in an amount of about 3 % by weight relative to the total amount of anacetrapib product. DMAP originates from 2′-(chloromethyl)-5-ethyl-4-fluoro-2-mothoxy-4′-trifluoromethyl)biphenyl (EBFCI) representing an impurity which forms in the preparation path of 2′-(chloromethyl)-4-fluoro-5-isopropyl-2-methoxy-4′-(trifluoromethyl)biphenyl under the above described conditions.

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

Reference£º
Patent; LEK Pharmaceuticals d.d.; EP2468736; (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.

1.10 g (4.67 mmol) of (4-isoquinolin-4-ylphenyl)methanol, obtained in step 10.1., are dissolved in 10 ml of chloroform and 1.4 ml (19 mmol) of thionyl chloride are added dropwise. The mixture is stirred at ambient temperature overnight and the filtrate is concentrated to dryness under reduced pressure. The residue is coevaporated with two times 10 ml of dichloroethane. The residue is taken up in 15 ml of tetrahydrofuran. 0.56 g (5.54 mmol) of 1,3-oxazolidine-2,4-dione are added, followed dropwise by a solution of 1.60 g (13.9 mmol) of 1,1,3,3-tetramethylguanidine in 5 ml of tetrahydrofuran. The mixture is heated at reflux overnight. It is cooled to ambient temperature. 20 ml of iced water and 100 ml of ethyl acetate are added. After they have settled, the phases are separated. The organic phase is washed with three times 10 ml of water and 20 ml of saturated aqueous sodium chloride solution. It is dried over sodium sulphate and the filtrate is concentrated under reduced pressure. The residue is purified by chromatography on silica gel, eluting with a 50/50 then 40/60 mixture of cyclohexane and ethyl acetate. This gives 0.84 g of product in the form of a solid yellow foam. m.p. ( C.): 65 C.

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

Reference£º
Patent; Sanofi-Aventis; US2006/14830; (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.131685-53-5,(R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone,as a common compound, the synthetic route is as follows.

To a solution of S-(+)-4-benzyl-3-propionyl-2-oxazolidinone (100 mg, 429 mumol) in CH2Cl2 (3.0 mL),TiCl4 (60 muL) and N,N,N?N?-tetramethylethylenediamine (160 muL, 1.07 mmol) were added at 0 C under Ar. Cinnamaldehyde (60 muL, 470 mumol) was added and the mixture was stirred at 0 C for 90 min. A saturated NH4Cl aqueous solution (1.0 mL) was added and the suspension was filtered through a Celite pad under suction. After the filtrate was suspended in H2O (15 mL), it was extracted with EtOAc (20 mL ¡Á2).The combined organic solution was washed with brine, dried over MgSO4, and then concentrated in vacuo. Silica gel column chromatography of the residue (EtOAc:hexane = 30:70) gave the aldol adduct (30.0 mg, 85%) as a white, amorphous solid. 1H-NMR (CDCl3) delta 1.26 (3H, d, J = 7.0 Hz), 2.71 (1H, dd, J = 9.5, 13.5Hz), 2.79 (1H, d, J = 7.3 Hz, exchangeable), 3.28 (1H, dd, J = 3.4, 13.5 Hz), 4.15 (1H, dd, J = 3.4, 9.5 Hz), 4.20 (1H, t, J = 9.1 Hz), 4.47 (1H, ddd, 1.0, 7.3, 14.3 Hz), 4.70 (1H, m), 6.29 (1H, dd, J = 7.3, 16.0 Hz), 6.67 (1H, dd, J = 1.0, 16.0 Hz), 7.16-7.41 (10H, aromatic protons). The 1H-NMR spectrum is in accordance with the spectrum reported by Evans.4, 131685-53-5

The synthetic route of 131685-53-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Ito, Atsushi; Kumagai, Ikuya; Maruyama, Miku; Maeda, Hayato; Tonouchi, Akio; Nehira, Tatsuo; Kimura, Ken-Ichi; Hashimoto, Masaru; Tetrahedron Letters; vol. 57; 10; (2016); p. 1117 – 1119;,
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.

Step 2: (S)-tert-Butyl 4-((4-bromo-2-chIoro-6-methylphenoxy)methyl)-2,2- dimethyIoxazolidine-3-carboxylate (23). To a solution of compound 22 (4 g, 18 mmol), intermediate 2 (4.8 g, 21.7 mmol) and triphenylphosphine (7.0 g, 27 mmol) in DCM (80 mL) was added diisopropylazodicarboxylate (5.4 g, 27 mmol). The reaction mixture was stirred at RT for 3 h. Water was added and the product was extracted with DCM. Purification by flash column chromatography gave the desired product 23 (5.8 g, 73%)., 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
Patent; EXELIXIS, INC.; XU, Wei; (106 pag.)WO2017/4608; (2017); 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

a) (S)-2,2-Dimethyl-4-((R)-3,3,3-trifluoro-2-hydroxy-propyl)-oxazolidine-3-carboxylic acid tert- butyl ester and (S)-2,2-Dimethyl-4-((S)-3,3,3-trifluoro-2-hydroxy-propyl)-oxazolidine-3- carboxylic acid tert-butyl esterTo 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 0 C 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. HC1 (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 (Si02; 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, 147959-19-1 (S)-tert-Butyl 2,2-dimethyl-4-(2-oxoethyl)oxazolidine-3-carboxylate 10586317, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; GALLEY, Guido; NORCROSS, Roger; POLARA, Alessandra; WO2011/57973; (2011); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem