Heterocyclic Building Blocks-Oxazolidine

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