Day: August 18, 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1121-83-1,5,5-Dimethyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

The synthesis of 5,5-Dimethyl-oxazolidin-2-one as depicted in the above scheme followed the procedures disclosed in: Bull, S. D.; Davies, S. G.; Jones, S.; Sanganee, H. J. J. Chem. Soc. Perkin Trans. 1 1999, 4, 387.To a 250 mL dry round bottom flask were added 5,5-dimethyl-oxazolidin-2-one (5.10 g, 44.3 mmol), triphosgene (5.26 g, 17.7 mmol) and anhydrous THF (80 mL). The mixture was stirred in an ice-water bath, then triethylamine (8.6 mL, 62.0 mmol) was added slowly. The resulting mixture was stirred at room temperature overnight. The reaction mixture was filtered and the filtrate was concentrated. To the residue was added 2,6-difluoro-4-hydroxybenzaldehyde (5.03 g, 31.9 mmol) and 80 mL of CH2Cl2. The resulting solution was cooled in an ice-water bath, then triethylamine (6.0 mL, 42.5 mmol) was added. After stirring at room temperature for 7 hours, water (100 mL) was added to the reaction mixture. The CH2Cl2 layer was separated, and the aqueous layer was extracted continually with CH2Cl2 (50 mL¡Á3). The combined CH2Cl2 solution was dried over Na2SO4. After removal of the solvent, the residue was purified with a silica gel chromatography (heptane/ethyl acetate, gradient eluting) to give 3,5-difluoro-4-formylphenyl 5,5-dimethyl-2-oxooxazolidine-3-carboxylate (6.9 g) as a pale yellow crystal. Yield: 52%. 1H NMR (CDCl3, 300 MHz): delta=10.39 (s, 1H), 7.09 (d, J=9.0 Hz, 2H), 3.97 (s, 2H), 1.67 (s, 6H).

The synthetic route of 1121-83-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; WARNER CHILCOTT COMPANY, LLC; US2011/98251; (2011); 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.90319-52-1,(R)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

Step A: Preparation of (R)-3-cinnamoyl-4-phenyloxazolidin-2-one: A THF (50 mL) solution of (R)-4-phenyloxazolidin-2-one (5.90 g, 36.2 mmol) was cooled to -78 ¡ãC and treated with lithium bis(trimethylsilyl)amide (36.9 mE, 36.9 mmol, 1.0 M in THF) dropwise over 15 minutes. After 15-minute stirring at -78 ¡ãC, a TFTF (10 mL) solution of cinnamoyl chloride (6.33 g, 38.0 mmol) was then introduced. The mixture was stirred for 1 hour at -78 ¡ãC and 2 hours at ambient temperature before it was quenched with saturated NaHCO3 (50 mL) and stirred for 1 hour. The mixture was diluted with EtOAc (200 mL), washed with water and brine, dried over MgSO4, filtered and concentrated to give the product as a pale yellow solid (10.6 g, 99.9percent yield). MS (apci) mlz = 293.9 (M+H).

The synthetic route of 90319-52-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BRANDHUBER, Barbara, J.; KERCHER, Timothy; KOLAKOWSKI, Gabrielle, R.; WINSKI, Sharon, L.; WO2014/78323; (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.90319-52-1,(R)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

Pivaloyl chloride (0.572 g, 4.74 mmol) was added dropwise to a solution of acid 12 (0.500 g, 4.31 mmol) in THF (15mL) at ?20¡ãC. After 1h, 4-(R)-phenyloxazolidinone (13) (2.06g, 12.6 mmol) and LiCl (0.201 g, 4.74 mmol) were added in one portion, and the reaction was warmed to room temperature and stirred overnight. The reaction was diluted with H2O (5mL) and extracted with EtOAc (3¡Á10mL). The combined organic layers were washed with satd aq NaHCO3 (2¡Á5mL), brine (1¡Á5mL), dried (Na2SO3), and concentrated under reduced pressure. The residue was purified via flash column chromatography eluting with hexanes/EtOAc (1:1) to give 0.983 g (87percent) of 14 as a white solid: mp=70?71¡ãC; 1H NMR (CDCl3, 300MHz) delta 7.49 (ddd, J=15.4, 2.0, 2.0Hz, 1H), 7.35 (comp, 5H), 7.07 (ddd, J=15.6, 4.4, 4.4Hz, 1H), 5.51 (dd, J=8.7, 4.1Hz, 1H), 4.73 (dd, J=8.7, 8.7Hz, 1H), 4.30 (dd, J=8.7, 3.8Hz, 1H), 4.14 (dd, J=4.6, 2.0Hz, 2H), 3.42 (s, 3H); 13C NMR (CDCl3, 300MHz) delta 164.4, 153.8, 146.8, 139.3, 129.3, 128.8, 126.2, 120.4, 71.6, 70.2, 58.9, 57.9; MS (CI) m/z 261 [C14H15NO4 (M) requires 261].

The synthetic route of 90319-52-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Hethcox, J. Caleb; Shanahan, Charles S.; Martin, Stephen F.; Tetrahedron; vol. 71; 37; (2015); p. 6361 – 6368;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

99395-88-7, (S)-4-Phenyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To (4S)-4-phenyl-l,3-oxazolidin-2-one (10) (0.405 g, 2.48 mmol, 1 equiv) in DCM (3.00 mL) cooled to 0 C was added a solution of triethyloxonium tetrafluoroborate (1.41 g, 7.44 mmol, 3 equiv) in DCM (3.00 mL). The mixture was allowed to warm slowly to rt and stirred for 18 h. The mixture was diluted with EtOAc (20 mL) and poured slowly over a cooled (0 C) solution of saturated aqueous NaHCC (25 mL). The layers were separated, and the aqueous layer was extracted with EtOAc (2 x 20 mL). The combined organic layers were washed with brine, dried over Na2SC>4, filtered, and concentrated to afford (4S)-2-ethoxy-4-phenyl-4,5- dihydro-l,3-oxazole (17) (0.428 g, 90%): 1HNMR (CDC13) delta: 7.38-7.28 (m, 5H), 5.15 (dd, 1H), 4.47 (dd, 1H), 4.42-4.35 (m, 2H), 4.20 (t, 1H), 1.41 (t, 3H) ppm; MS: (m/e): 192 (M+l).

As the paragraph descriping shows that 99395-88-7 is playing an increasingly important role.

Reference£º
Patent; PURDUE PHARMA L.P.; BLAKE, Paul; TAFESSE, Laykea; (85 pag.)WO2017/192858; (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

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).

As the paragraph descriping shows that 147959-19-1 is playing an increasingly important role.

Reference£º
Patent; LUDWIG-MAXIMILIANS-UNIVERSITAET MUENCHEN; WO2006/94770; (2006); A2;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

497-25-6, Oxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-Fluoro-2-(2-oxooxazolidin-3-yl)benzonitrile. A 48 mL pressure vessel containing 2-bromo-4-fluorobenzonitrile (1.00 g, 5.00 mmol), 2-oxazolidone (0.390 g, 4.50 mmol), K2CO3 (0.970 g, 7.0 mmol) and xantphos (0.231 g, 0.40 mmol) in dioxane (10 mL) was degassed with argon for 15 inn. Pd2 dba3 (0.140 g, 0.15 mmol) was introduced and then the reaction mixture was heated at 70 C. for 18 h. The mixture was cooled, diluted with dioxane, and then filtered through Celite. The resulting mixture was concentrated in vacuo and subjected to column chromatography on silica gel with hexanes:ethyl acetate (1:1) to (3:7) gradient as the eluent to afford the title compound as a white solid (0.460 g, 50% yield): 1H NMR (400 MHz, CDCl3) delta ppm: 7.73 (1H, dd, J=5.8, 8.6 Hz), 7.43 (1H, dd, J=2.5, 9.6 Hz), 7.11 (1H, ddd, J=2.5, 7.5, 8.7 Hz), 4.60 (2H, t, J=7.1 Hz), 4.29 (2H, t, J=7.1 HJz); LCMS (+EST, M+H+) m/z 207.

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Reference£º
Patent; Bristol-Myers Squibb Company; US2007/129379; (2007); 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.184363-66-4,(S)-4-Phenyl-3-propionyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

(S) -4-benzyl-3-propionyloxazolidinone (16.5 g, 1.1 eq)Was dissolved in 40 ml of dichloromethane, cooled to 0 C,A solution of titanium tetrachloride (14 g, 1.1 eq) in dichloromethane was added dropwise,After the drop, keep stirring below 0 C for 10 min.Diisopropylethylamine (9.7 g, 1.1 eq) was added dropwise,After the drop, keep stirring below 0 C for 30 min. The compound (II-b) (30 g, 1 equiv)Dissolved in methylene chloride, added dropwise to the reaction system,After the dropwise addition, the mixture was stirred at 20 to 25 C for 10 hours.To the reaction system, an aqueous solution of saturated ammonium chloride was added,Extracted with dichloromethane, and the resulting organic phases were washed with water and water, respectivelyWashed with saturated brine and dried over anhydrous sodium sulfate.The solvent was removed by evaporation under reduced pressure to give the crude product. The crude product was purified by column chromatography,To give the title compound (IV-a) (33.9 g, yield 91%).HPLC detection, no enantiomeric detection, that is, chiral purity of 100%.

The synthetic route of 184363-66-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Zhejiang Yongning Pharmaceutical Co., Ltd.; Ye Tianjian; Lu Xiuwei; Yu Guangliang; Liu Ting; (14 pag.)CN105085322; (2017); B;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

99395-88-7, (S)-4-Phenyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 4. (5)-3-((5)-3-(4-Chlorophenyl)-3-(6-methoxypyridin-3-yl)propanoyl)-4- phenyloxazolidin-2-one (0330) (0331) To a precooled (0 C) solution of (5)-3-(4-chlorophenyl)-3-(6-methoxypyidin-3- yl)propanoic acid (3.30 g, 1 1.3 mmol) in THF (30.0 mL) was added pivolyl chloride (1.39 mL, 1 1.3 mmol), DMAP (cat) and triethylamine (3.15 mL, 22.6 mmol) drop-wise and stirred for 1 h. In another precooled (-78 C) suspension of (5)-4-phenyloxazolidin-2-one (2.03 g, 12.4 mmol) in THF (10.0 mL) was added w-BuLi (2.50 M solution in hexanes, 9.30 mL, 14.9 mmol) drop- wise and stirred at -20 C for 1 h. The solution of the above mixed anhydride was added slowly and stirred for additional 3 h. The reaction mixture was quenched with saturated solution of NH4CI (250 mL) and extracted with EtOAc (2 x 200 mL). The combined EtOAc extracts were washed with brine (200 mL), dried ( a2S04), filtered and concentrated under reduced pressure. The residue was purified on 40 g S1O2 column using using a gradient elution of 0-40% EtOAc in hexanes. Fractions containing the product were combined and concentrated under reduced pressure to provide the the title product. MS: m/z = 437 (M+H)+.

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

Reference£º
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; WILLIAMS, Peter, D.; MCCAULEY, John, A.; BUNGARD, Christopher, J.; BENNETT, David Jonathan; WADDELL, Sherman, T.; MORRIELLO, Gregori, J.; CHANG, Lehua; DWYER, Michael, P.; HOLLOWAY, M. Katharine; CRESPO, Alejandro; CHU, Xin-Jie; WISCOUNT, Catherine; LOUGHRAN, H. Marie; MANIKOWSKI, Jesse, J.; SCHULZ, Jurgen; KEERTIKAR, Kartik, M.; HU, Bin; ZHONG, Bin; JI, Tao; WO2015/138220; (2015); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

90719-32-7, (S)-4-Benzyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-Dimethylaminopyridine (2.55 g, 21.3 mmol) and triethylamine (46.9 ml, 340.8 mmol) in dichloromethane (100 ml) are added to a solution of (S)-(-)-4-benzyl-2-oxazolidinone (37.7 g, 213 mmol) in dichloromethane (300 ml). Next, isovaleroyl chloride (33.75 ml, 207 mmol) in dichloromethane (50 ml) is added to the previously prepared mixture and cooled to 0 C. keeping the internal temperature below 10 C. The reaction mixture is stirred for 30 minutes at 10 C., then the formed salts are filtered. Water (100 ml) is added and the phases are separated. The organic phase is washed with water (100 ml) and brine (100 ml), dried over sodium sulphate and evaporated to dryness obtaining 53 g of a yellow oil, which solidifies over time (yield 95%). 1H NMR (300 MHz, CDCl3, 298K) delta 7.35-7.15 (m, 5H), 4.71-4.61 (m, 1H), 4.21-4.10 (m, 2H), 3.35-3.25 (dd, J=13.2, J=3.4 Hz.1H), 2.85-2.72 (dd, J=14.97 Hz, 6.8 Hz, 1H), 2.80-2.67 (m, 2H), 2.29-2.12 (sept, J=13.2 Hz.1H), 1.03-0.98 (d, J=6.8 Hz.3H), 0.98-0.95 (d, J=6.8 Hz, 3H). 13C NMR (75 MHz, CDCl3, 298K) delta 175.6, 171.2, 154.4, 137.1, 130.5, 130.2, 126.0, 82.1, 66.1, 45.6, 42.6, 41.4, 34.0, 28.7, 27.3, 19.7.

The synthetic route of 90719-32-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Chemo Iberica, S.A.; Taddei, Maurizio; Russo, Adele; Cini, Elena; Riva, Renata; Rasparini, Marcello; Carcone, Luca; Banfi, Luca; Vitale, Romina; Roseblade, Stephen; Zanotti-Gerosa, Antonio Carlo; US2013/71899; (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.108149-63-9,(R)-tert-Butyl 4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate,as a common compound, the synthetic route is as follows.

General procedure: To a stirred solution of 6 (0.100 g, 0.433 mmol), appropriate substituted phenol (0.649 mmol) and PPh3 (0.182 g,0.693 mmol) in anhydrous toluene (5 mL) was added DIAD(0.14 mL, 0.693 mmol) at 80 C. After 3 h, EtOAc (40 mL)was added to the resulting solution. The organic layer was washed with 0.5 M aqueous NaOH (40 mL) and water (2 X40 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash silica gel column chromatography eluting with Hexanes/EtOAc (9:1) or (95:5) to afford compounds 7a-s.

The synthetic route of 108149-63-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Andrade, Saulo F.; Campos, Edmar F.S.; Teixeira, Claudia S.; Bandeira, Cristiano C.; Lavorato, Stefania N.; Romeiro, Nelilma C.; Bertollo, Caryne M.; Oliveira, Monica C.; Souza-Fagundes, Elaine M.; Alves, Ricardo J.; Medicinal Chemistry; vol. 10; 6; (2014); p. 609 – 618;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem