Heterocyclic Building Blocks-Oxazolidine

A heterogeneous catalyst is a catalyst that is present in a different phase than the reactants. Such catalysts generally function by furnishing an active surface upon which a reaction can occur. 80-65-9, name is 3-Aminooxazolidin-2-one, introduce a new downstream synthesis route as follows., 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

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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);,
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One of the major reasons is to use measurements of the macroscopic properties of a system, the rate of change in the concentration of reactants or products with time, to discover the sequence of events that occur at the molecular level. 695-53-4, introduce a new downstream synthesis route., 695-53-4

Preparation of 2-[3-(1-adamantyl)-2-(5,5-dimethyl-2,4-dioxooxazolidinyl)-3-oxopropanamido]-4-nitroanisole [5] A suspension of 16.28 g (0.04 mol) of [4], 5.17 g (0.04 mol) of 5,5-dimethyloxazolidine-2,4-dione, and 16.58 g (0.12) mol of anhydrous potassium carbonate in 380 mL of dried acetone was refluxed for 3 hours. Thin layer chromatographic analysis indicated that the reaction was complete. The reaction mixture was concentrated in vacuoto yield an orange-colored solid. It was dissolved in ethyl acetate and the organic layer was washed with HCl (10%) and brine until neutrality. The organic layer was dried, filtered, and concentrated to yield an oil which solidified upon standing. It was triturated in ligroin. The final dried product (15.92 g, 79.8%) gave one spot on TLC. All analytical data confirmed the assigned structure., 695-53-4

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Patent; EASTMAN KODAK COMPANY; EP1014186; (2000); A1;,
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95715-86-9, The molecularity of an elementary reaction is the number of molecules that collide during that step in the mechanism. If there is only a single reactant molecule in an elementary reaction, that step is designated as unimolecular. 95715-86-9, name is Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate. A new synthetic method of this compound is introduced below.

95715-86-9, 4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (12b); A 250-ml two-necked flask was equipped with a magnetic stirring bar, reflux condenser bearing a drying tube and a dropping funnel. The flask was charged with tetrahydrofuran (100 ml) and lithium aluminium hydride (2.16 g, 57.0 mmol). While the suspension in the flask was stirred, a solution of the ester 12a (9.90 g, 38.2 mmol) in THF (50 ml) was added dropwise during 20 min. The reaction was monitored by thin layer chromatography. When the reaction was finished, the mixture was cooled in an ice bath and a solution of 10% potassium hydroxide (20 ml) was added dropwise during 10 min. The mixture was stirred for 2 h at room temperature, whereafter the white precipitate was removed by filtration through celite. The combined organic filtrates were washed with 100 ml of aqueous phosphate buffer (pH 7), and the aqueous layer was extracted with ether. The combined organic phases were dried and concentrated which gave the title compound (8.3 g, 94%). The residue was used without further purification.

In every case, we must determine the overall rate law from experimental data and deduce the mechanism from the rate law (and sometimes from other data). you can also browse my other articles about 95715-86-9 if you are interested.

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Patent; MEDIVIR AB; WO2008/107365; (2008); A1;,
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16251-45-9, One of the major reasons is to use measurements of the macroscopic properties of a system, the rate of change in the concentration of reactants or products with time, to discover the sequence of events that occur at the molecular level. 16251-45-9, introduce a new downstream synthesis route.

2a (4S,5R)-3-(Bromoacetyl)-4-methyl-5-phenyloxazolidin-2-one Production is carried out analogously to Example 1a) starting from (4S,5R)-4-methyl-5-phenyloxazolidin-2-one. The coverage of NMR is identical to 1a)., 16251-45-9

There are, however, a few established termolecular elementary reactions. The reaction of nitric oxide with oxygen appears to involve termolecular steps. you can also browse my other articles about16251-45-9

Reference£º
Patent; KLAR, ULRICH; SCHWEDE, WOLFGANG; SKUBALLA, WERNER; BUCHMANN, BERND; US2003/144523; (2003); A1;,
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108149-63-9, We know that the rate of many reactions can be accelerated by catalysts. A catalyst speeds up the rate of a reaction by lowering the activation energy; in addition, the catalyst is regenerated in the process. 108149-63-9, name is (R)-tert-Butyl 4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate,below Introduce a new synthetic route.

General procedure: To a stirred solution of 39 (0.100g, 0.433mmol), appropriate substituted phenol (0.649mmol) and PPh3 (0.182g, 0.693mmol) in anhydrous toluene (5mL) was added DIAD (0.14mL, 0.693mmol) at 80C. After 3h, EtOAc (40mL) was added to the resulting solution. The organic layer was washed with 0.5M aqueous NaOH (40mL) and water (2¡Á40mL), 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)., 108149-63-9

Other significant industrial processes that involve the use of heterogeneous catalysts include the preparation of sulfuric acid, the preparation of ammonia, the oxidation of ammonia to nitric acid, and the synthesis of methanol. 108149-63-9, if you are interested, you can browse my other articles.

Reference£º
Article; Andrade, Saulo F.; Oliveira, Barbara G.; Pereira, Larissa C.; Ramos, Jonas P.; Joaquim, Angelica R.; Steppe, Martin; Souza-Fagundes, Elaine M.; Alves, Ricardo J.; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 13 – 25;,
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#REF!

(4R)-3-[(2Z)-[4-[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1-oxo-2-buten-1-yl]-4-phenyl-2-oxazolidinone (7) To a solution of acid 6 (6.0 g, 28.2 mmol) in THF (40 mL) at -78 C., was added triethylamine (4.00 mL, 28.2 mmol) followed by trimethylacetyl chloride (3.46 mL, 28.2 mmol) drop-wise. The mixture was warmed to 0 C. over 20 minutes, then the anhydride mixture was cooled to -78 C. Separately, to a solution of (R)-(+)-phenyl-2-oxazolidione (Aldrich) (4.60 g, 28.2 mmol) in THF (40 mL) at -78 C. was carefully added n-BuLi (2.50 M in THF, 11.3 mL, 28.2 mmol) and the mixture was stirred (30 minutes) then transferred to the anhydride solution at -78 C. The final reaction mixture was warmed to room temperature and stirred (over night). The mixture was diluted with EtOAc (200 mL), washed (H2O and brine), dried (Na2SO4), and purified by silica gel column chromatography (hexanes:EtOAc) to yield 7 as a colorless oil (10.2 g, 100% yield). 1H NMR (400 MHz, CDCl3) delta 7.36-7.20 (m, 5H), 7.10 (dt, J=11.6, 2.6 Hz, 1H), 6.50 (dt, J=12.0, 4.6 Hz, 1H), 5.44 (dd, J=8.8, 4.0 Hz, 1H), 4.68-4.59 (m, 3H), 4.22 (dd, J=8.8, 4.0 Hz, 1H), 0.85 (s, 9H), 0.00 (s, 6H). 13C NMR (100 MHz, CDCl3) delta 169.3, 160.6, 158.8, 144.3, 134.5, 134.0, 131.0, 122.0, 75.2, 67.9, 62.8, 31.1, 23.4, 0.00. ESI (+VE) m/z: 384.1 (M+Na)+. HR-ESI cacld for C19H28NO4Si (M+Na)+: 362.1782, Found: 362.1789.

Other significant industrial processes that involve the use of heterogeneous catalysts include the preparation of sulfuric acid, the preparation of ammonia, the oxidation of ammonia to nitric acid, and the synthesis of methanol. 90319-52-1, if you are interested, you can browse my other articles.

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Patent; The United States of America, as represented by the Secretary, Department of Health & Human Services; Burke, Jr., Terrence R.; Liu, Fa; Lee, Kyung S.; Park, Jung-Eun; (182 pag.)US10266565; (2019); B2;,
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Example-20: Preparation of (R)-4-phenyI-3-propionyIoxazolidin-2-one (Formula B-I) ( )-4-phenyloxazolidin-2-one (100 gm) and dimethylaminopyridine (10 gm) were added to a mixture of propionic acid (50 gm) and toluene (400 ml) at 25-30C. Cooled the reaction mixture to 0-5C, dicyclohexylcarbodiimide (151.5 gm) was slowly added and stirred the reaction mixture for 1 hr at the same temperature. Slowly raised the temperature of the reaction mixture to 25-30C and stirred for 14 hrs at the same temperature. Filtered the reaction mixture, aqueous hydrochloric acid solution was added to the filtrate and stirred the reaction mixture for 20 min at the same temperature. Both the organic and aqueous layers were separated and washed the organic layer with aqueous HC1 solution followed by with aqueous sodium bicarbonate solution and then with aqueous sodium chloride solution. Distilled off the solvent completely from the organic layer under reduced pressure and co- distilled with cyclohexane under reduced pressure. Cyclohexane (200 ml) was added to the obtained solid at 55-60C and stirred for 15 min at the same temperature. Cooled the reaction mixture to 25-30C and stirred for 40 min at the same temperature. Filtered the solid, washed with cyclohexane and dried to get the title compound. Yield: 124.0 gm. M.R: 81-82C., 90319-52-1

Other significant industrial processes that involve the use of heterogeneous catalysts include the preparation of sulfuric acid, the preparation of ammonia, the oxidation of ammonia to nitric acid, and the synthesis of methanol. 90319-52-1, if you are interested, you can browse my other articles.

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Patent; MSN LABORATORIES PRIVATE LIMITED; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; VENKAT REDDY, Ghojala; WO2015/87351; (2015); A2;,
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A heterogeneous catalyst is a catalyst that is present in a different phase than the reactants. Such catalysts generally function by furnishing an active surface upon which a reaction can occur. 2346-26-1, name is Oxazolidine-2,4-dione, introduce a new downstream synthesis route as follows., 2346-26-1

WORKING EXAMPLE 1 A mixture of 3-methoxy-4-(2-phenyl-4-oxazolylmethoxy)cinnamaldehyde (5.5 g), 2,4-oxazolidinedione (6.7 g), piperidine (1.4 g) and acetic acid (120 ml) was stirred for three days under reflux. The reaction mixture was cooled, and resulting crystalline precipitate was collected by filtration, which was washed with water, ethanol and isopropyl ether, successively to give 5-[3-methoxy-4-(2-phenyl-4-oxazolylmethoxy)cinnamylidene]-2,4-oxazolidinedione (2.9 g, 43%), which was recrystallized from chloroform-methanol to afford yellow needles, m.p.227-228 C.

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Patent; Takeda Chemical Industries, Ltd.; US5932601; (1999); A;,
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139009-66-8, The molecularity of an elementary reaction is the number of molecules that collide during that step in the mechanism. If there is only a single reactant molecule in an elementary reaction, that step is designated as unimolecular. 139009-66-8, name is (S)-N-Boc-2,2-dimethyloxazolidine-4-carboxylic Acid. A new synthetic method of this compound is introduced below.

Isobutyl chloroformate (2.51 g; 2.40 mL; 18.36 mmol) and triethylamine (2.25 g; 3.10 mL; 22.24 mmol) were added to a cold (0 C) solution of aminoacetal 2c from the previous step (?3.35 g; 14.27 mmol) in dichloromethane (11 mL) under an argon atmosphere. The reaction mixture was vigorously stirred for 30 min at 0 C, then ethanethiol (2.01 g; 2.40 mL; 32.41 mmol) and triethylamine (2.25 g; 3.10 mL; 22.24 mmol) were added. The resulting solution was stirred for 30 min at 0 C and 45 min at rt. The reaction mixture was diluted with dichloromethane (25 mL), washed with water (40 mL) and brine (30 mL), dried over anhydrous MgSO4, concentrated under reduced pressure and purified by distillation under reduced pressure (bp 110 C/0.3 mmHg) to give 2.19 g (53% over three steps) of thioester 5, as white crystals.

In every case, we must determine the overall rate law from experimental data and deduce the mechanism from the rate law (and sometimes from other data). you can also browse my other articles about 139009-66-8 if you are interested.

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Article; Trajkovic, Milos; Ferjancic, Zorana; Saicic, Radomir N.; Tetrahedron Asymmetry; vol. 23; 8; (2012); p. 602 – 604;,
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An elementary termolecular reaction involves the simultaneous collision of three atoms, molecules, or ions.(R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one, cas is 145589-03-3. Here is a downstream synthesis route of the compound 145589-03-3. 145589-03-3

Intermediate 15: [(R)-4-BENZVL-3- (2-HYDROXYMETHYL-3-METHVL-BUTANOYL)-OXAZOLIDINONE] [4-BENZYL-3- (3-METHYLBUTANOYL)-OXAZOLIDINONE] (14) * (26. 1g, 0.1mol) was stirred in dry [DICHLOROMETHANE (400ML)] at [0C] under nitrogen as titanium tetrachloride (1. 0M solution in dichloromethane, 105ml, 0. [105MOL)] was added and the mixture, which contained a yellow precipitate, was stirred a further 15 minutes then [DIISOPROPYLETHYLAMINE (19ML, 0. 11MOL)] was added dropwise, maintaining the temperature below [5C.] The resulting purple solution was stirred for 75 minutes then 1,3, 5-trioxane (9.9g, [0.] 11mol) in [DICHLOROMETHANE] (60ml) was added, and after a further 10 minutes, titanium tetrachloride (1. [OM] in DCM, 105ml, 0. [105MOL)] was added. The mixture was stirred for 2.5 hours at [0C] then quenched by the addition of saturated ammonium chloride (500ml). Water (100ml) and [DICHLOROMETHANE] [(100ML)] were added, the aqueous phase extracted with a further 2 x [100ML DICHLOROMETHANE,] the combined organics dried over [NA2SO4] and evaporated. Recrystallisation from 30% [DICHLOROMETHANE/PETROLEUM] gave 18.7g (64%) of the title compound as a white solid. LCMS RT=2.94minutes [MH+ 292], 145589-03-3

Other significant industrial processes that involve the use of heterogeneous catalysts include the preparation of sulfuric acid, the preparation of ammonia, the oxidation of ammonia to nitric acid, and the synthesis of methanol. 145589-03-3, if you are interested, you can browse my other articles.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2003/104200; (2003); A1;,
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