Month: August 2020

2346-26-1, Oxazolidine-2,4-dione is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 1.0 g (4.02 mmol) of 2-(4-[(4-chlorophenyl)oxy]phenyl)ethanol, prepared in accordance with Example 14.1., and 1.1 ml (7.89 mmol) of triethylamine in 12 ml of dichloromethane, cooled by an ice bath, is admixed with a solution of 0.60 g (5.24 mmol) of methanesulphonyl chloride in 2 ml of dichloromethane. The combined solutions are subsequently stirred at ambient temperature for 2 hours. They are diluted with 25 ml of water and 75 ml of dichloromethane. After the phases have settled and been separated, the organic phase is washed with 25 ml of water then 25 ml of saturated aqueous sodium chloride solution, dried over sodium sulphate and evaporated to dryness, to give 1.32 g of product in the form of an oil. The product is redissolved in 12 ml of tetrahydrofuran. 0.50 g (5 mmol) of 1,3-oxazolidine-2,4-dione and a solution of 0.92 g (8.0 mmol) of 1,1,3,3-tetramethylguanidine in solution in 4 ml of tetrahydrofuran are added. The mixture is subsequently heated at reflux overnight. It is cooled with an ice bath and 25 ml of an aqueous 0.1N solution of hydrochloric acid and 100 ml of ethyl acetate are added. After the phases have settled, the organic phase is separated off and washed with two times 25 ml of water then with 25 ml of saturated aqueous sodium chloride solution, dried over sodium sulphate and evaporated to dryness. The residue is purified by chromatography on silica gel, eluting with an 85/15 then 75/25 and 65/35 mixture of cyclohexane and ethyl acetate, to give 1.20 g of product in the form of a white solid. Melting point ( C.): 105-107

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

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.99395-88-7,(S)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

The compound of formula II (250 g, 1.53 mol) was added to toluene (3750 mL)Heat to 70 degrees. Sodium methoxide methanol solution (29 wt%, 314 g, 1.68 mol) was added dropwise.Plus End, atmospheric distillation of methanol. Cooled to 0-5 C,The compound of formula III (364.4 g, 1.68 mol)Temperature is not higher than 20 . Add finished, the reaction 1-2 hours.After the reaction was completed, water (250 mL) was added, heated to 50-60 C, allowed to stand for delamination and the aqueous phase was separated.The organic phase is washed twice with water. The organic phase was concentrated to give the crude product.The crude product was beaten with n-hexane (1500 mL), filtered and dried to obtain the intermediate of formula IV.Yield: 436g, yield: 95.4%

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

Reference£º
Patent; (11 pag.)CN107573304; (2018); A;,
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

A solution of LiOH (0.046 g, 1.928 mmol) in water (2 mL) was added to a solution of (S)-3-tert-butyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate (0.5 g, 1.928 mmol) in THF (6 mL). The resulting mixture was stirred at rt for 48 h, acidified to pH 4 with a 1 N aqueous solution of hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases were dried (MgS04), filtered and concentrated under vacuum to afford Cap L-25 (0.2 g) as a yellow oil. Used without further purification.XH NMR (400MHz, DMSO-d6, mixture of rotomers) delta 12.72 (br. s., 1H), 4.33 – 4.23 (m, 1H), 4.18 – 4.09 (m, 1H), 3.93 (dt, J=9.0, 3.3 Hz, 1H), 1.56 – 1.51 (m, 3H), 1.42 (s, 7H), 1.39 – 1.33 (m, 6H);13C MR (101MHz, DMSO-d6, mixture of rotomers) delta 172.32 – 171.83 (m), 150.7, 93.76 – 93.42 (m), 79.66 – 79.01 (m), 65.94 – 65.54 (m), 58.79 – 58.57 (m), 28.05 – 27.74 (m, 3C), 24.93 – 24.75 (m), 24.16 – 23.99 (m)

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (2015); 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

[0061] An oven-dried 500 milliliter (mL) Schlenk flask was cooled under nitrogen gas (N2)and then charged with (S)-4-isopropyloxazolidin-2-one (7.05 grams (g), 54.6 millimoles (mmol))and anhydrous THF (300 mL). After sealing with a rubber septum, the resulting colorless solutionwas cooled to -78 C in a dry ice/acetone bath and treated with a solution of n-BuLi (2.5 Molar (M)in hexanes , 24.0 mL, 60.0 mmol). The reaction mixture was stirred at -78 C for 30 minutes (mm)and treated with via syringe with 3-phenylpropanyl chloride (8.80 mL, 59.2 mmol). The resultingyellow solution was stirred for 2.5 hours (h) at -78 C, the cold bath was removed, a solution of saturated aqueous ammonium chloride (NH4C1, 100 mL) was added, and the resulting white suspension was allowed to stir at room temperature for 10 mm. The crude reaction mixture was extracted with ethyl acetate (EtOAc, 3 xl 00 mL), and the combined organic extracts were washed with saturated aqueous sodium chloride solution (NaC1, brine, 100 mL), dried over anhydrous sodium sulfate (Na2SO4), filtered, and concentrated by rotary evaporation. The crude concentrate was purified via column chromatography (silica gel (Si02), 1-30% acetone in hexanes) to give the title compound (11.4 g, 80%) as a white solid: mp 59 – 62 C; ?H NMR (400 MHz, CDC13) oe 7.33 -7.16 (m, 5H), 4.44-4.39 (m, 1H), 4.24 (dd,J= 9.1, 8.1 Hz, 1H), 4.19 (dd, J= 9.1, 3.2 Hz, 1H),3.32 (ddd, J= 16.9, 8.6, 6.7 Hz, 1H), 3.22 (ddd, J= 16.9, 8.0, 7.2 Hz, 1H), 3.06 – 2.92 (m, 2H),2.35 (pd, J= 7.0, 3.9 Hz, 1H), 0.90 (d, J= 7.0 Hz, 2H), 0.84 (d, J= 7.0 Hz, 2H); ?3C NMR (101MHz, CDC13) oe 172.40, 154.06, 140.49, 128.56, 128.46, 126.24, 63.40, 58.45, 37.07, 30.45, 28.39,17.97, 14.64; ESIMS m/z 262 ([M+H]j.

As the paragraph descriping shows that 17016-83-0 is playing an increasingly important role.

Reference£º
Patent; DOW AGROSCIENCES LLC; BOEBEL, Timothy A.; LU, Yu; MEYER, Kevin G.; YAO, Chenglin; DAEUBLE, John F.; BRAVO-ALTAMIRANO, Karla; NUGENT, Benjamin M.; (237 pag.)WO2016/7529; (2016); A1;,
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

C. 4-[4-(2,4-Dioxo-oxazolidin-5-ylidenemethyl)-2-methoxy-phenoxy]-naphthalene-1 – carboxylic acid methyl ester; . A mixture of 4-(4-Formyl-2-methoxy-phenoxy)- naphthalene-1 -carboxylic acid methyl ester (33.6 mg, 0.10 mmol), thiazolidine- 2,4-dione (14.3 mg, 0.11 mmol), sodium acetate (24.6 mg, 0.30 mmol), piperidine (1 drop) and ethanol (2 ml_) /acetonitrile (4 ml_) was heated at reflux overnight. The solvent was evaporated to ~ 2 ml_ volume. After cooling to room temperature, the precipitate was collected by filtration and washed with acetonitrile and water. 1H NMR (400 Hz, DMSO-c/6) ?8.91 (d, 1 H), 8.40 (d, 1 H), 8.08 (d, 1 H), 7.73 (t, 1 H), 7.65 (t, 1 H), 7.4 (d, 1 H), 7.35 (s, 1 H), 7.28 (d, 1 H), 7.21 (d, 1 H), 6.60 (d, 1 H), 3.87 (s, 3H), 3.73 (s, 3H); LC/MS (m/z) [M+1]+ 436.3 (calculated for C23Hi8NO6S, 436.1 ).

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

Reference£º
Patent; JANSSEN PHARMACEUTICA N.V.; WO2008/109727; (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.95530-58-8,(R)-4-Isopropyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

A cooled (-20 C) solution of tiglic acid (2.005 g, 20.031 mmol) in anhydrous tetrahydrofuran (50 mL) was sequentially treated with triethylamine (6.1 mL, 44.068 mmol) and dropwise pivaloyl chloride (2.7 mL, 22.034 mmol). After stirring at -20 C for 30 min, lithium chloride (1.019 g, 24.037 mmol) and (R)-(+)-4-isopropyl-2-oxazolidinone (2.587 g, 20.031 mmol) were added. The reaction mixture was allowed to slowly warm to room temperature, stirred for 3 days and was then quenched with saturated ammonium chloride. The aqueous layer was extracted with ethyl acetate (2 x). The organics were combined, dried over anhydrous sodium sulfate, filtered and the volatiles were removed in vacuo. The residue was purified by silica gel chromatography using a 50 g Isolute cartridge eluted with a continuous gradient of iso- hexanes/ethyl acetate 1 :0 to 4:1 to afford the title compound (3.307 g, 78%) as a colourless solid. 1H NMR (300 MHz, CDCl3): delta 0.92 (d, J = 6.9 Hz, 3H), 0.94 (d, J = 7.1 Hz, 3H), 1 .83 (d, J = 6.9 Hz, 3H), 1.93 (s, 3H), 2.38 (d of heptet, J = 6.9, 4.2 Hz, 1 H), 4.19 (dd, J = 8.9, 4.6 Hz, 1 H), 4.33 (app t, J = 8.9 Hz, 1 H), 4.49-4.58 (m, 1 H), 6.23 (q, J = 7.1 Hz, 1 H)

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

Reference£º
Patent; GILEAD SCIENCES, INC.; SELCIA LIMITED; ACIRO, Caroline; STEADMAN, Victoria Alexandra; PETTIT, Simon Neil; POULLENNEC, Karine G.; LAZARIDES, Linos; DEAN, David Kenneth; DUNBAR, Neil Andrew; HIGHTON, Adrian John; KEATS, Andrew John; SIEGEL, Dustin Scott; KARKI, Kapil Kumar; SCHRIER, Adam James; JANSA, Petr; MACKMAN, Richard; WO2013/185103; (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.80-65-9,3-Aminooxazolidin-2-one,as a common compound, the synthetic route is as follows.

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.

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

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.

To a suspension of (E)-3-(1,4-dimethyl-1H-benzo[d][1,2,3]triazol-5-yl)acrylic acid (82 g, 376 mmol) in tetrahydrofuran (1.5 L) was added triethylamine (131 mL, 939 mmol). The reaction mixture was cooled to -25 C and pivaloyl chloride (46 ml, 376 mmol) was added dropwise and stirred for 30 min at -25 C. Lithium chloride (17.52 g, 413 mmol) was added in one- portion, followed by (S)-4-phenyloxazolidin-2-one (58.8 g, 361 mmol) and the reaction mixture was allowed to warm to ambient temperature and was stirred for 1 hr. The mixture was cooled to -25 C and pivaloyl chloride (12ml, 98 mmol) was added dropwise and allowed to stir for an additional 1 hr. THF (300 mL) was added followed by (S)-4- phenyloxazolidin-2-one (10 g, 61 mmol) and pivaloyl chloride (18 ml, 147 mmol) and the mixture was stirred at 10 C for 1 hr and then ambient temperature for 18 hr. The reaction mixture was diluted with ethyl acetate (1 L) and washed with 5% NaHSO3 (1 L). The resulting solid was collected by filtration and washed with water and diethyl ether to afford a light yellow solid (S,E)-3-(3-(1,4-dimethyl-1H-benzo[d][1,2,3]triazol-5-yl)acryloyl)-4- phenyloxazolidin-2-one (104.39 g, 288 mmol, 77 % yield).1H NMR (DMSO-d6) delta: 8.05 (d, J=15.8 Hz, 1H), 7.71-7.88 (m, 3H), 7.30-7.45 (m, 5H), 5.61 (m, 1H), 4.83 (m, 1H), 4.30 (s, 3H), 4.24 (m, 1H), 2.78 (s, 3H). LC-MS: m/z = 363.2 [M+H]+.

99395-88-7 (S)-4-Phenyloxazolidin-2-one 730424, aoxazolidine compound, is more and more widely used in various.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CALLAHAN, James Francis; COLANDREA, Vincent J.; COOPER, Anthony William James; GOODWIN, Nicole Cathleen; HUFF, Chelsea Ariane; KARPIAK, Joel; KERNS, Jeffrey K.; NIE, Hong; (404 pag.)WO2018/109647; (2018); 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

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).; (4S)- 4- [(2R)- 2- Hydroxy- 3- nitrorhoropyl]-2,2- dimethyloxazolidine- 3-carboxylic acid tert-butyl ester (12): A solution of indabox ligand (+)-16 (493 mg, 1.375 mmol) and Cu(OAc)2-H2O (250 mg, 1.25 mmol) in EtOH (37.5 mL) was stirred for I h at room temperature. Nitromethane (13.6 mL, 250.0 mmol) and the aldehyde 6 (6.08 g, 25.0 mmol) were subsequently added to the resulting clear blue solution. After stirring for 5 d at room temperature the solvent was removed in vacuo. The diastereomeric ratio 12:13 was determined by HPLC analysis (n-heptane/i-PrOH 99:1; LiChrospher 250×4, Si 60, 5 mum; EPO 1.5 mL/min; 215 nm; 13: tr = 33.8 min; 12: tr = 42.4 min) of the crude reaction mixture to be 97:3. The crude product was purified by flash chromatography on silica gel (/?-hexane:EtOAc 3:1) to give 12 (6.87 g, 94%) as a 97:3 mixture of diastereomers. For analytical purposes a small quantity of the diastereomers was separated by preparative HPLC (?-heptane/z-PrOH 99:1; Hibar 250×25, Si 60, 5 mum, 15 mL/min; 215 nm) to afford 12 as a colorless solid: mp 61-62 C; [alpha]22D +28.9 (c O.56, CH2Cl2); IR (KBr): 3483 cm”1, 1697, 1558, 1394; 1H NMR (500 MHz, C2D2Cl4, 100 0C): delta 1.50 (s, 9 H), 1.51 (s, 3 H), 1.60 (s, 3 H), 1.82-1.94 (m, 2 H), 3.48 (bs, 1 H), 3.79 (dd, J= 1.2, 9.1 Hz, 1 H), 4.02 (dd, J= 6.1, 9.1 Hz, 1 H), 4.06-4.14 (m, 1 H), 4.35-4.42 (m, 1 H), 4.42-4.50 (m, 2 H); 13C NMR (100 MHz, C2D2Cl4, 100 0C): delta 24.2 (CH3), 27.3 (CH3), 28.5 (CH3), 38.8 (CH2), 54.7 (CH), 66.8 (CH), 68.1 (CH2), 80.7 (CH2), 80.9 (C), 94.1 (C), 152.6 (C); MS (CI) m/z (rel. intensity): 305 (1) [M+H]+, 188 (100); Anal. Calcd for C13H24N2O6: C, 51.31 ; H, 7.95; N, 9.20. Found: C, 51.31; H, 7.93; N, 9.04.

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.

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.145589-03-3,(R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one,as a common compound, the synthetic route is as follows.

Under N2 protection,500mL three flask, compound 4 (26.83g, 102.7mmol) was dissolved In 80mL ofanhydrous THF a low temperature (-50 C) was added dropwise with 1.0M LiHMDS(110mL, 110 mmol), After the addition was complete, -50 C under stirring for1h, and then added dropwise 1,3-dimethyl-3,4,5,6-tetrahydro-2- Pyrimidone(DMPU) (28.95g, 225.8mmol), the addition was complete the mixture was stirredat -50 C under 0.5h After the addition of cis-2-butene-1,4-dibromo-5 (8.78g,41.0mmol) in 18mL anhydrous THF, Stirred for 1h at -50 C, the naturallywarmed to 0 C, kept at 0 C 1h, then rose to 5-10 C insulation 1.5h, TLCplate track points to the end of the reaction. With 50mL of saturated solutionof NH4Cl quench the reaction, Rotary evaporation to remove THF, (30mL ¡Á 3) theaqueous phase was extracted with ethyl acetate, the combined EA phases werewashed with 1M (50mL ¡Á 4) EA dilute HCl rinse with about three times, driedover anhydrous MgSO4, spin-dry, drain the solvent, The crude product wasrecrystallized from methanol. To give a white crystalline solid was 20.72g,namely the title compound 2.3, Yield 88%.

The synthetic route of 145589-03-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ZHEJIANGHISOAR PHARMACEUTICAL CO., LTD; PAN, XIANHUA; LIU, FENG; LI, HONGMING; HUANG, RUI; LI, YIMING; ZHANG, QUNHUI; DENG, FEI; CHEN, WENBIN; (21 pag.)CN103059012; (2016); B;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem