Heterocyclic Building Blocks-Oxazolidine

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

[0528] General Procedure for Goldberg Reaction [0529] This protocol was performed according to conditions disclosed in Org. Lett. 2003, 5 (7), 963. [0530] To a suspension of copper(I) iodide (0.354 g, 1.86 mmol), potassium carbonate (7.35 g, 53.2 mmol) and (¡À)-trans-1,2-diaminocyclohexane (0.328 ml, 2.67 mmol) in dioxane, (15 ml) 9 (5 g, 26.7 mmol) and 10b (2.352 g, 27.01 mmol) were added and the reaction mixture was stirred at 100 C. for 20 h. Reaction mixture was cooled and filtered through silica gel pad with the help of EtOAc (150 ml). Filtrate was concentrated in vacuo to 11b 4.7 g (91%) [0531] Analogous coupling reactions performed according to the above procedure and utilising the appropriate coupling partners according to the schemes gave the following yields: 11a (81%), 11c (40%), 11d (55%), 24a (74%), 24b (64%) [0532] *The above reaction also works under the microwave conditions at 110 C. in 4 h to give 11 (50-90%).

As the paragraph descriping shows that 497-25-6 is playing an increasingly important role.

Reference£º
Patent; Cambridge Enterprise Limited; Kapadnis, Prashant Bhimrao; Glen, Robert; Hiley, Robin; Bell, James; Spring, David; US2013/53372; (2013); 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, Intermediate 46:2-[(frans-4-hydroxycyclohexyl)amino]-6-{[6-(2-oxo-1 ,3-oxazolidin-3-yl)-1 ,3- benzothiazol-2-yl]amino}-4-pyridinecarbaldehyde Under an atmosphere of nitrogen, a mixture of 2-[(6-bromo-1 ,3-benzothiazol-2-yl)amino]- 6-[(trans-4-hydroxycyclohexyl)amino]-4-pyridinecarbaldehyde [intermediate 44] (100mg, 0.224mmol) , 1 ,3-oxazolidin-2-one (58.4mg, 0.671 mmol), caesium carbonate (146mg, 0.45mmol) and copper(l) iodide (85mg, 0.45mmol) in dry Nu,Nu-dimethylformamide (3ml_) was thoroughly degassed by the repeated alternate application of vacuum and nitrogen pressure, then treated with Nu,Nu’-dimethylethylenediamine (0.095ml_, 0.89mmol) and heated at 1 10C for 1 hour. The mixture was cooled to ambient temperature, filtered and evaporated to dryness. The product was purified by chromatography on silica from 0 to 15% methanol in dichloromethane to afford the title compound (98mg, 0.216mmol, 97% yield). LCMS (Method A): Rt 0.78 minutes; m/z 454 (MH+).

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

Reference£º
Patent; GLAXO GROUP LIMITED; ALDER, Catherine Mary; BALDWIN, Ian Robert; BARTON, Nicholas Paul; CAMPBELL, Amanda Jennifer; CHAMPIGNY, Aurelie Cecile; HARLING, John David; MAXWELL, Aoife Caitriona; SIMPSON, Juliet Kay; SMITH, Ian Edward David; TAME, Christopher John; WILSON, Caroline; WOOLVEN, James Michael; WO2011/110575; (2011); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

452339-73-0, (R)-5-(2,2-Dimethyl-4H-benzo[d][1,3]dioxin-6-yl)oxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of (5R)-5-(2, 2-dimethyl-4H-1, 3-benzodioxin-6-yl)-1, 3-oxazolidin-2-one (Example 1 viii) (503mg) in DMF (10mL) was treated with sodium hydride (60% dispersion in mineral oil) (97mg) under nitrogen for 20 min. A solution of 1-[2-(benzyloxy) ethoxy] -4- (2-bromoethyl) benzene (676mg) in DMF (5 mL) was added and the reaction stirred for a further 2 h. The reaction mixture was concentrated in vacuo then the residue was prified by chromatography (Biotage, 40g) eluting with EtOAc-petroleum ether (2: 3) to give the title compound (585mg). LCMS RT = 3.66 min

452339-73-0, 452339-73-0 (R)-5-(2,2-Dimethyl-4H-benzo[d][1,3]dioxin-6-yl)oxazolidin-2-one 10933894, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2003/91204; (2003); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

95530-58-8,95530-58-8, (R)-4-Isopropyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of (R)-4-isopropyl-oxazolidin-2-one (1.3g, 10 mmol) and NaH (480 mg, 60% oildispersion, 12 mmol) in THF (50 ml) was stirred at rt for 2h. then cooled to 0C. A solution ofbromoacetonitrile (1.4 ml, 20 mmol) in THF (30 ml) was added slowly to the reaction mixture. Theresulting mixture was stirred at rt for overnight. The mixture was treated with small amount of waterand then the mixture was passed through a silica pad. The filtrate was concentrated and the residue20 was subjected to a short column to give the crude product. The process was repeated and bothcrude product were combined and further purified by another short column to give the product(3.3g).To a solution of above product (3.3g, 19 mmol) in THF (40 ml) at ooc was added a solution ofBH3THF in THF (1M, 200 ml). The resulting mixture was stirred at ooc for 30 min. then at rt for 4h.25 The mixture was then cooled to ooc again and treated with cold HCI (6 N, 20 ml) to strong acidic pH.The organic solvent was removed under reduced pressure. The residue was treated with NaOH (4 N,-40 ml) to pH>10, then extracted with EtOAc (5 x 80 ml) and DCM (5 x 80 ml). The combined extracts from both solvent were dried (Na2S04) and concentrated. EtOAc concentrate afford 1.9 gdesired product (not clean) and 650 mg of cleaner product was obtained from the DCM concentrate.A mixture of above product (1.9 g, 11 mmol), 3-bromo-6-fluoro-imidazo[1,2-b]pyridazine (650mg, 3 mmol), and triethylamine (1.5 ml) in isopropyl alcohol (8 ml) was heated in a microwave at5 140C for 20 min. twice. The reaction mixture was concentrated and the residue was subjected toISCO (40 g column), to gave the titled compound (345 mg). LRMS (ESI) mjz 368 and 370.2 [(M+H)]+,calc’d for C14H1sBrN502: 368.24.B

As the paragraph descriping shows that 95530-58-8 is playing an increasingly important role.

Reference£º
Patent; LEXICON PHARMACEUTICALS, INC.; BI, Yingzhi; CARSON, Kenneth Gordon; CIANCHETTA, Giovanni; GREEN, Michael Alan; KUMI, Godwin; LIANG, Zhi; LIU, Ying Jade; MAIN, Alan; ZHANG, Yulian; ZIPP, Glenn Gregory; WO2013/134219; (2013); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

80-65-9, 3-Aminooxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

80-65-9, General procedure: Following the addition of 4-(4-fluorophenoxy) butyric acid (0.71 g, 3.6 mmol) to 20 mL ofdichloromethane in a 50 mL three-necked round-bottom flask, thesolution was agitated until dissolution. Subsequently, EDCI (0.85 g,4.44 mmol) HOBt (0.6 g, 4.44 mmol) and triethylamine (0.84 g,9.25 mmol) were added in turn at 0 C. Stirring in an ice bath for 1 h,3-amino-2-oxazolidinone (0.37 g, 3.6 mmol) was added again. Thesolutionwas brought to 25 C and stirred overnight. Following TLC,the product was filtered by vacuum and dried under rotary evaporation.The product was a white solid weighing 0.51 g with a yieldof 50.2%.

80-65-9 3-Aminooxazolidin-2-one 65725, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Article; Jiang, Kai; Yan, Xinlin; Yu, Jiahao; Xiao, Zijian; Wu, Hao; Zhao, Meihua; Yue, Yuandong; Zhou, Xiaoping; Xiao, Junhai; Lin, Feng; European Journal of Medicinal Chemistry; vol. 194; (2020);,
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 (R) -4-isopropyloxazolidin-2-one (25.0g, 0.194mol, 1.0eq) in anhydrous THF (1150 mL) was added n-BuLi (85.0 mL, 0.213mol, 1.1eq) at -78 under N2and the mixture was stirred at the same temperature for 1 h, a large number of white solids formed. Then propionyl chloride (20.0 mL, 0.232mol, 1.2eq) was added at -78 and the mixture was stirred at the same temperature for 1 h. After the consumption of (S) -4-isopropyloxazolidin-2-one monitored by TLC, the solution was poured into saturated ammonium chloride solution (1.2 L) and the mixture was extracted with EA (700 mL, 350 mL ¡Á 2) . The organic extract was washed with 1.0 N NaOH solution (1.0 L) and brine (1.0 L) , dried over anhydrous sodium sulfate, filtered, concentrated in vacuo and purified by SiO2column chromatography (PE : EA = 10: 1) to give the title compound as a colorless oil (32.6 g, 90.8%) . ESI m/z: calcd for C9H17NO3[M+H]+: 186.1, found 186.1.1H NMR (400 MHz, CDCl3) delta 4.48 -4.37 (m, 1H) , 4.27 (t, J = 8.7 Hz, 1H) , 4.21 (dd, J = 9.1, 3.1 Hz, 1H) , 3.04 -2.82 (m, 2H) , 2.45 -2.30 (m, 1H) , 1.17 (t, J = 7.4 Hz, 3H) , 0.90 (dd, J = 17.1, 7.0 Hz, 6H) .

95530-58-8 (R)-4-Isopropyloxazolidin-2-one 641505, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; HANGZHOU DAC BIOTECH CO. LTD; ZHAO, Robert Yongxin; YANG, Qingliang; HUANG, Yuanyuan; ZHAO, Linyao; GAI, Shun; YE, Hangbo; LEI, Jun; XU, Yifang; CAO, Mingjun; GUO, Huihui; JIA, Junxiang; TONG, Qianqian; LI, Wenjun; ZHOU, Xiaomai; XIE, Hongsheng; BAI, Lu; CAI, Xiang; ZHUO, Xiaotao; ZHANG, Xiuzheng; ZHENG, Jun; (424 pag.)WO2019/127607; (2019); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

95715-86-9, Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,95715-86-9

Referring to FIG. 12, the synthesis of D-threo-PPMP may be via stereoselective addition of phenyl cuprate to D-Gamer aldehyde. The syn adduct, which leads to the D-threo isomer, will be the major product. The minor L-erythro isomer (approximately 5%) can be removed by crystallization from chloroform at the late stage of the synthesis. Synthesis starts with a four-step synthetic procedure for the production of D-Garner Aldehyde from D-serine. We have synthesized L-Gamer Aldehyde from L-serine at the kilogram scale utilizing the same method for the production of safingol. Garner Aldehyde was obtained in 28% overall yield at 98+% ee purity without chromatography. Phenyl cuprate will be generated in situ by the reaction of copper(I) iodide and phenyl magnesium bromide. The addition of phenyl cuprate to D-Garner Aldehyde will yield intermediate 6. The deprotection of intermediate 6 with HCl produces D-threo-1-phenyl-2-amino-propane-1,3-diol-7. The intermediate 7 is reacted with activated palmitic acid and followed by base hydrolysis to form intermediate 8. The primary hydroxy group of intermediate 8 will be converted to the mesylate, and then substituted with morpholine to yield the final product D-threo-PPMP. Our synthetic plan is an efficient, practical synthesis to the enantiomerically pure PPMP. Most of the reactions described have been successfully conducted at the kilogram scale in our kilo lab. It is anticipated that the initial 2 g bach can be delivered within 6 to 8 weeks after the desired PPMP enantiomer is identified. Modifications to the current method of synthesis and other methods of synthesis of D-threo-PPMP are readily known to one of skill in the art.

The synthetic route of 95715-86-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Maurer, Barry James; Reynolds, Charles Patrick; US2005/101674; (2005); 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, Step 7: Synthesis of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[[2-(4-fluoro-2-methoxy-5-propan-2- ylphenyl)-5-(trifluoromethyl)phenyl]methyl]-4-methyl- 1, 3-oxazolidin-2-one (anacetrapib); 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 biaryl 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 HCI (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 (EtOAc/hexanes) 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-(trifluoromethyl) 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-methoxy-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.

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

95715-86-9, Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

95715-86-9, In stageA harvesting (R) -2,2- dimethyl – oxazolidine-3,4-dicarboxylic acid 3-t- butyl ester 4-methyl ester (11.4g, 44.0mmol) was dissolved in dichloromethane (100mL), added at -78 Diisopropyl aluminum hydride (1.5M in toluene, 66mL). The temperature was raised to room temperature and stirred for 18 hours. After completion of the reaction, methanol (20 mL) and sodium hydroxide (1N, 200mL) was slowly added to the organic solution is then extracted with methylene chloride, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was separated by column chromatography the title compound were harvested (9.7g, 95%).

As the paragraph descriping shows that 95715-86-9 is playing an increasingly important role.

Reference£º
Patent; LG Life Sciences Ltd.; Park, Heui Sul; Koo, Sun Young; Kim, Hyoung Jin; Lee, Sung Bae; Kwak, Hyo Shin; Artemov, V.; Kim, Soon Ha; (34 pag.)CN105636956; (2016); A;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

95715-86-9,95715-86-9, Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation of (S)-2-amino-/V-(7-ethoxy-4-(3,4,5-trimethoxybenzyl)isoquinolin-8-yl)-3- hvdroxypropanamide dihydrochloride 26 (S)-3-( e/t-Butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acidTo a solution of methyl (S)-3-terf-butyl 4-methyl 2,2-dimethyloxazolidine-3,4- dicarboxylate (0.35 g, 1 .35 mmol) in THF (10 mL) in a 50 mL round-bottomed flask equipped with a magnetic stirrer was added a solution of LiOH monohydrate (62 mg, 1 .48 mmol) in H2O (5 mL) and the mixture was stirred overnight at RT. THF was evaporated at 40C under vacuum and the residue was diluted with H2O (25 mL) before acidification with 3% aqueous HCI to pH = 4. The solution was extracted with Et2O (3×50 mL) and the organic layers were combined, washed with brine (20 mL), dried over Na2SO4, filtered and concentrated at 40C under vacuum to give (S)-3- (fe/t-butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid CCH 34168-1 as a colorless oil (147 mg, 44% yield).CCH 34168-1MW: 469.4; Yield: 21 %; Colorless oil.

The synthetic route of 95715-86-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; EXONHIT S.A.; LEBLOND, Bertrand; TAVERNE, Thierry; BEAUSOLEIL, Eric; CHAUVIGNAC, Cedric; CASAGRANDE, Anne-Sophie; DESIRE, Laurent; WO2011/151423; (2011); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem