Tag: M.W:300-400

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.153652-70-1,(4S,5R)-3-Benzoyl-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid,as a common compound, the synthetic route is as follows.

Solution of 2-CHLOR-4, 6-dimethoxy-1,3, 5-triazine (0.175 g, 1 mmole) in 5 ML THF was mixed with N-METHYLMORPHOLINE (D ML, 1 mmole) for 30 minutes at temperature of 0- 5C, to form respective quaternary TRIAZINILAMMONIUM salt. Then, phenyl isoserine of the formula 4b, where R3= R4=CH3 (0 325 g, 1 MMOL) was added and mixed for 12 hours, first at temperature of 0-5C, next at room temperature. N-METHYLMORPHOLINE was filtered off and solvent was removed from the filtrate. It gave respective triazine ester of the formula 6b, where R3=R4=CH3, R5=R6=OCH3, with the quantitative yield. TLC : ELUENT CHCI3, RF=0. 50 ‘H-NMR (COCI3) : 5= 1.76 (s, 3H); 1.79 (s, 3H); 3.76 (s, 6H); 5.20 (d, J= 7.5 Hz, 1H) ; 5.59, (d, J= 7.5 Hz, 1 H) ; 7.43-7. 56 (m, 8H) ; 7.70-7. 43 (m, 2H) [ppm]. IR (KBr): 1790 [CM~1] The triazine ester was coupled with protected Baccatin (it of generalized formula 3, where R2=Si (C2HS) 3, in the presence of magnesium bromide and diazobicycloundekane. It gave 0.945 g of the final product (93.8%) with the melting temperature of 171-173C. TLC: eluent (acetone: benzene 1: 4), RF=0. 85 1H-NMR (CDCI3) : 6=0. 55 (q, J=8. 5 Hz, 6H); 0.94 (t, J=8.5 Hz, 9H); 1.17 (s, 3H) ; 1.22 (s, 3H); 1.67 (s, 3H); 1.77 (s, 1H) ; 1.83-1. 85 (m, 1H) ; 1.87 (s, 3H); 1.94 (s, 3H); 2.02 (s, 3H); 2.07 (s, 3H); 2.02-2. 18 (m, 2H); 2.19 (s, 3H); 2.07-2. 20 (m, 2H); 2.48-2. 50 (m, 2H); 3.77 (d, J=7.5 Hz, 1H) ; 4.07 (d, J=8.5 Hz, 1H) ; 4.25 (d, J=8.5 Hz, 1H) ; 4.42-4. 46 (m, 1H) ; 4.58 (d, J=7.5 HZ, 1H) ; 4.88-4. 93 (m, 1H) ; 5.28 (d, J=6. 5 Hz, 1H) ; 5.68 (d, J=7.5 Hz, 1H) ; 6.21- 6.25 (m, 1H) ; 6.49 (s, 1H) ; 6.91-6. 96 (m, 1H) ; 7.07-7. 22 (m, 8H); 7.44-7. 48 (m, 2H) ; 7.61- 7.65 (m, 1 H) ; 8.02 (d, J=7.5 Hz, 2H) [ppm] The product of condensation was treated with formic acid in THF, and the final product was CHROMATOGRAPHICALLY PURIFIED on silica gel with the system of hexane: ethyl acetate 2: 1. It gave 0.621 G (yield 76%) of a product spectroscopically and CHROMATOGRAPHICALLY identical to Paclitaxel., 153652-70-1

153652-70-1 (4S,5R)-3-Benzoyl-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid 10131335, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; AGROPHARM S.A.; WO2004/56790; (2004); A1;,
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

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, To a solution of (45′,5J?)-5-[3}5-bis(trifluoromethyl)phenyl]-4-methyl-li3-oxazoIidin-2-one (4.94 g, 15.77 mmol) in THF (75 mL) was added NaH (60% dispersion in mineral oil) (0.526 g, 13.14 mmol). After stirring the reaction at room temperature for 10 minutes, 3-bromo-2- (bromomethyl)-6-chloropyridine (3.0 g, 10.51 mmol) was added as a solution in THF (20 mL). The reaction was stirred at room temperature for 16 hours and then quenched with saturated NH4CI (40 mL). The mixture was diluted with EtOAc (100 mL) and hexanes (50 mL). The organic layer was washed with water (2 x 100 mL) and brine (50 mL), dried over Na2S0 , filtered, and concentrated. Purification of the residue by flash chromatography on silica gel with 0 to 50% EtOAc/hexanes afforded (4555^)-5-[3,5-bis(trifiuoromethyl)phenyl]-3-t(3-bromo-6- chloropyridin-2-yl)methyl]-4-methyl-1,3-oxazolidin-2-one. LCMS = 518.8 (M+H)+ 1H MR (CD<, 500 MHz) delta 7.90 (s, 1H), 7.81-7.83 (m, 3H), 7.18 (d, J- 8.5 Hz, 1H), 5.87 (d, J- 8.5 Hz, 1H), 5.02 (d, J= 17.2 Hz, 1H)5 4.42 (m, IE), 4.32 (d, J= 17.1 Hz, 1H), 0.80 (d, J= 6.6 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
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.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.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

875444-08-9,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.

N-Chlorosuccinimide (10.4 g, 78.1 mmol) was added to a stirred solution of acetaldoxine (3.55 g, 60.1 mrnol) in dry DMF at 00C under N2. The reaction was allowed to warm to room temperature and was stirred for 3 h. Water (100 rnL) was added and the mixture was extracted with Et2O (4 x 80 rnL). The combined extracts were washed with water (50 rnL) and brine (50 mL), dried (Na2SO4) and concentrated in vacuo to afford N-hydroxyethanimidoyl chloride, as a colorless oil. 1H NuMR (500 MHz, CDCl3): delta 8.96 (br s, IH), 2.26 (s, 3 H).Triethylamine (123.4 mg, 170 muL, 1.21 mmol) was added to a stirred solution of (4,S,5.R)-5-[3,5- bis(trifluoromethyl)phenyl]-3-[3-(4-fluoro-5-isopropyl-2-methoxyphenyl)prop-2-yn-l-yl]-4-methyl-l,3- oxazolidin-2-one (21.9 mg, 0.0423 mmol) and N-hydroxyethanimidoyl chloride (124.4 mg, 1.33 mmol) in dry toluene (2 mL) at room temperature under N2. The reaction was heated at reflux for 2 days. The reaction mixture was cooled to room temperature, diluted with IN HCl and extracted with EtOAc (3 x 20 mL). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 12 x 160 mm, 0-30% EtOAc in hexanes gradient) to afford (45,5Lambda)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[5-(4-fluoro-5-isopropyl-2-methoxyphenyl)-3- methylisoxazol-4-yl]methyl}-4-methyl-l,3-oxazolidin-2-one. ^= 0.38 (20% EtOAc/hexanes). LCMS calc. = 575.2; found = 575.3 (M+l)+. 1H NMR (600 MHz, CDCl3): delta 7.84 (s, 1 H); 7.64 (s, 2 H); 7.31 (d, J= 8.3 Hz, 1 H); 6.68 (d, J= 11.8 Hz, 1 H); 5.27 (d, J= 8.0 Hz, 1 H); 4.78 (d, J= 15.6 Hz, 1 H);4.00 (d, J= 15.6 Hz, 1 H); 3.82 (s, 3 H); 3.72-3.68 (m, 1 H); 3.22-3.16 (m, 1 H); 2.38 (s, 3 H); 1.24 (d, J= 7.0 Hz, 3 H); 1.22 (d, J = 7.0 Hz, 3 H); 0.42 (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 fields.

Reference£º
Patent; MERCK & CO., INC.; WO2007/81569; (2007); 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, (45,5R)-5-[3,5-Z?w(trifluoromethyl)phenyl]-4-methyl-l,3-oxazolidin-2-one (400 mg, 1.28 mrnol) was treated with NaH (60% in oil, 128 mg, 3.2 mmol) and 2-(bromomethyl)-l-iodo-4- (trifluoromethyl)benzene (Example 70, 466 mg, 1,28 mmol) as described in Example 66 to afford (45,5i.)-5-[3,5-Akappa(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]-4-methyl-l,3- oxazolidin-2-one as a white solid. LCMS = 598.0 (M+l)+. lH NMR (CDCI3, 500 MHz): delta 8.06 (d, J=8.2 Hz, 1 H), 7.93 (s, 1 H), 7.82 (s, 2 H), 7.61 (s, 1 H), 7.33 (dd, J= 8.2, 1.4 Hz, 1 H), 5.79 (d, J= 7.8 hz, 1 H), 4.91 (d, J= 16 Hz, 1 H), 4.40 (d, J= 16 Hz, 1 H), 4.16-4.06 (m, 1 H), 0.83 (d, J= 6.4 Hz, 3 H).

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

Reference£º
Patent; MERCK & CO., INC.; WO2007/79186; (2007); 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.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, iNTERMEDIATE 29 (4S,5R?)-5- 13 ,5-Bis(trifluoromethyl)phenyl] -3- F(5-bromo-2-chloropyridin-4-yl)methyll -4-methyl- 1 ,3-oxazolidin-2-oneA solution of (4S,5R)-5- [3 ,5-bis(trifluoromethyl)phenyl] -4-methyl- 1,3 -oxazolidin-2-one(INTERMEDIATE 4, 1.305 g, 4.17 mmol) in 30 mL of DMF was cooled to -20C. NaHMDS(1.0 M, 4.17 ml, 4.17 mmol) was added and the reaction was stirrred at -20C for 20 minutes.Next, a solution of (5-bromo-2-chloropyridin-4-yl)methyl methanesulfonate (II?1TERMEDIATE28, 1.2522 g, 4.17 mmol) in 5 mL of DMF was added and the solution turned brown. Thereaction was warmed to 0C by switching to an ice/water bath and the reaction stirred for an additional 30 minutes, at which time an LCMS aliquot confirmed the reaction was complete. It was quenched with aqueous NaHCO3. The reaction was extracted with ethyl acetate, then washed with aqueous NaHCO3 and brine, dried with Na2SO4, filtered and the filtrate was concentrated. The crude oil was purified by silica gel chromatography to give the titledcompound as an off-white solid. ?H NMR (CDC13, 500 MHz): 8.52 (s, 1H), 7.92 (s, 1H), 7.80 (s, 2H), 7.36 (s, 1H), 5.81 (d, 1H), 4.78 (d, 1H), 4.34 (d, 1H), 4.17 (m, 1H), 0.82 (d, 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.; ACTON, John, J., III; YE, Feng; VACHAL, Petr; SHA, Deyou; DROPINSKI, James, F.; CHU, Lin; ONDEYKA, Debra; KIM, Alexander, J.; COLANDREA, Vincent, J.; ZANG, Yi; ZHANG, Fengqi; DONG, Guizhen; WO2013/165854; (2013); A1;,
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

Oxazolidinone III (9.58 g, 30.6 mmol), biaryl chloride II (10.83 g, 30.0 mmol), tetrabutylammonium iodide (0.02 molar equivalents, based on the amount of biaryl chloride), K2CO3 (2 equivalents), and DMF (12 mL) were charged to a 100 mL flask, and the resulting slurry was stirred at 60 C. for 17 hours. Then n-heptane and water were added at the same temperature. The aqueous layer was removed, and the organic layer was washed with water. The product was crystallized by cooling the organic mixture. Isolated crystals were washed with heptane and dried to afford 17.60 g of the titled compound (27.6 mmol, 92%).

As the paragraph descriping shows that 875444-08-9 is playing an increasingly important role.

Reference£º
Patent; Chung, Cheol K.; Humphey, Guy R.; Maligres, Peter E.; Wright, Timothy J.; US2014/303380; (2014); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem