Day: November 17, 2020

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. 131685-53-5, name is (R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone,below Introduce a new synthetic route., 131685-53-5

Example 15; Step 15A: Compound 15a; (S) -4-Benzyl-3-propionyl-oxazolidin-2-one (46.7 g, 200.0 mmol) was dissolved in THF (870 mL) under inert atmosphere (N2). This was then cooled to-70 C (dry ice/acetone) and treated with sodium hexamethyldisilazide-HMDS (110 mL of a 2. 0M solution in THF, 220.0 mmol) in a dropwise fashion (addition lasted for-45 min. ). The resulting mixture was stirred at-70 C for 1 h. A solution of 4-chlorobenzyl bromide (53.4 g, 260.0 mmol) in THF (160 mL) was then added dropwise over 30 min. The resulting mixture was stirred at-70 C for 6 h and then allowed to warm to room temperature overnight. The reaction was carefully quenched with H20 (100 mL) and the solvent was removed in vacuo. The resulting slurry was suspended in H20 (200 mL) and filtered. The solid was rinsed with EtOAc and air-dried to give 36. 67 g (102.6 mmol, 51%) of 15a. A second crop was obtained from the filtrates after the organic layer was separated, washed with brine, dried (MgS04) and evaporated. The resulting brown solid was suspended in MeOH and filtered to give 17.22 g (48.2 mmol, 24%) of 15a. Only one diastereomer was observed by IH NMR and by single crystal X-ray analysis. IH NMR (Cl3-300 MHz) b 1.18 (d, J = 6.3 Hz, 3H, ) ; 2.66-2. 56 (m, 2 H); 3.16-3. 07 (m, 2H); 4.22-4. 02 (m, 3H); 4. 71- 4.63 (m, 1H) ; 7.08-7. 05 (m, 2H); 7.32-7. 21 (m, 7H)., 131685-53-5

Any one of these steps may be slow and thus may serve as the rate determining step. In general, however, in the presence of the catalyst, the overall rate of the reaction is faster than it would be if the reactants were in the gas or liquid phase.

Reference£º
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2005/42516; (2005); A2;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

452339-73-0, 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. 452339-73-0, name is (R)-5-(2,2-Dimethyl-4H-benzo[d][1,3]dioxin-6-yl)oxazolidin-2-one. A new synthetic method of this compound is introduced below.

Sodium hydride (60% oil dispersion, 1.4g) was added to a stirred solution of (5R)- (2, 2- DIMETHYL-4H-1, 3-BENZODIOXIN-6YL)-1, 3OXAZOLIDIN-2-ONE (6. 0G) in dry dimethylformamide (80ML) at 0 under nitrogen. After 20 min a solution of 1- {4- [ (6-BROMOHEXYL) oxy] butyl}-4- iodobenzene (12.6g) in dry dimethylformamide (30ML) was added dropwise. The mixture was stirred for 15h at ambient temperature. The mixture was poured into an aqueous ammonium chloride solution (700MI) and extracted into ethyl acetate. The organic extracts were washed with water, dried (NA2SO4) and evaporated. Purification by chromatography on a biotage cartridge (90g) using ether-petroleum ether (40-60) (4: 1) gave the title compound as a clear oil (10G). LCMS RT = 4.19 min.

Any one of these steps may be slow and thus may serve as the rate determining step. In general, however, in the presence of the catalyst, the overall rate of the reaction is faster than it would be if the reactants were in the gas or liquid phase.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2004/39762; (2004); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

80-65-9, 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. 80-65-9, name is 3-Aminooxazolidin-2-one,below Introduce a new synthetic route.

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%.

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. 80-65-9, if you are interested, you can browse my other articles.

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
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99395-88-7, Rate laws may be derived directly from the chemical equations for elementary reactions. This is not the case, however, for ordinary chemical reactions.(S)-4-Phenyloxazolidin-2-one, cas is 99395-88-7, below Introduce a new synthetic route.

To a solution of (E)-4- (benzyloxy)but-2-enoic acid 236 (2.5g, 13.01mmol) and triethylamine (1.45g, 14.31 mmol) in anhydrous THF (40 mL) under nitrogen at -78 C was added trimethylacetyl chloride (1.72g, 14.3 lmmol). The reaction mixture was stirred at -78 C for 10 minutes, 0 C for 1 hour, then re-cooled to -78C.At the same time, in a seperate flask charged with a solution of (S)-4-phenyloxazolidin-2- one 237 (0.42g, 2.6mmol) in anhydrous THF (40 mL) under nitrogen at -78 C was added dropwise a solution of LiHMDS (14.31 mL, 14.3 lmmol). The mixture was stirred at -78 C for 20 minutes and then transferred via a cannula into the reaction flask containing the mixed anhydride at -78 C. The reaction mixture was stirred at 0 C for 1 hour, then warmed to room temperature and stirred for 18 hours. The crude mixture was quenched with sat. NH4CI (200 mL), and concentrated in vacuo, to about half of its original volume under reduced pressure to remove THF. The remaining mixture was extracted with ethyl acetate (150 mL x 2). The organic layer was separated, combined, dried over anhydrous Na2SC>4 and concentrated to dryness. The residue was purified by silica gel column (PE : EA = 2 : 1) to give 238, (S,E)-3-(4-(benzyloxy)but-2-enoyl)-4-phenyloxazolidin-2-one (3 g, 68% yield). LC-MS (LC method 1): m/z 338 (M+l)+., 99395-88-7

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. 99395-88-7, if you are interested, you can browse my other articles.

Reference£º
Patent; SPERO OPCO; LISTER, Troy; SHARMA, Rajiv; ZABAWA, Thomas; ZAHLER, Robert; (146 pag.)WO2017/189866; (2017); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

875444-08-9, 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. 875444-08-9, name is (4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one,below Introduce a new synthetic route.

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). 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. 875444-08-9, if you are interested, you can browse my other articles. 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

99395-88-7, Rate laws may be derived directly from the chemical equations for elementary reactions. This is not the case, however, for ordinary chemical reactions.(S)-4-Phenyloxazolidin-2-one, cas is 99395-88-7, below Introduce a new synthetic route.

The compounds of formula I 21.2g taken with 110ml of DMF was dissolved and replaced with nitrogen, cooled to -10 ~ 0 C under nitrogen, temperature control, input portionwise 16g of lithium hydride, insulation 0.5h, slowly dropwise methyl chloroformate 30.2g, control temperature -10 ~ 0 C, after the addition was complete insulation 1h, warmed to 20 ~ 25 C, into S-4- phenyl-2-oxazolidinone 15.5g, feeding ended, insulation, the reaction was complete, water and methyl tert-butyl ether extracts, standing layer, the organic layer was washed with saturated brine, evaporated under reduced pressure to give an oil. With a mixture of ethyl acetate and hexane to crystallize with stirring, suction filtered and washed with hexane, dried in vacuo to give a white solid product 38.8g, molar yield 92.9%, HPLC purity 95%. Without further purification, can be used directly in the next step., 99395-88-7

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. 99395-88-7, if you are interested, you can browse my other articles.

Reference£º
Patent; Zhejiang Jiuzhou Pharmaceutical Co., Ltd; ZHU, GUOLIANG; LI, YUNGUANG; YANG, LIJUN; SUN, LIGUO; CHEN, XIANGYUAN; (8 pag.)CN105461649; (2016); A;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

108149-63-9, 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. 108149-63-9, name is (R)-tert-Butyl 4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate. A new synthetic method of this compound is introduced below.

Serinol derivative 5 (2.8 g, 12.1 mmol) was dissolved in dry DMSO (30 mL) and treated with NaH (582 mg, 60% dispersion in mineral oil, 14.5 mmol) and mesylate 43 (4.8 g, 14.5 mmol) was added sequentially. The reaction immediately changed color from nearly colorless to orange red. The reaction was stirred at room temperature for 16 h, and was then quenched by the ice and diluted with ethyl acetate. The two layers were separated and the aqueous layer extracted with ethyl acetate (5 15 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo. Purification by flash column chromatography (85:15 petroleum ether/EtOAc) yielded the serinol ether 42 (4.01 g, 71%) as colorless oil:, 108149-63-9

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 about108149-63-9

Reference£º
Article; Das, Shyamsundar; Induvadana, Boddeti; Ramana; Tetrahedron; vol. 69; 7; (2013); p. 1881 – 1896;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

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.

A 3-necked, 1000 mL round-bottom flask fitted with a N2 inlet adapter, magnetic stir bar, drying tube, temperature guage, and a septa was charged with methyl (S)- (-)-3- (TERT-BUTOXYCARBONYL)-2, 2-DIMETHYL-4-OXAZOLIDINE-CARBOXYLATE (15. 42 g, 59.46 mmole) and 120 ML of anhydrous toluene. The solution was cooled TO-78 C in A dry ice/acetone bath. A solution of DIISOBUTYLALUMINUM hydride in toluene (69.5 ML, 104.1 mmole) was cooled TO-78 C in A separate dry ice/acetone bath and added to the ester solution under N2 pressure via a steel cannula over a period of 30 min. The rate of addition was adjusted to prevent the reaction mixture from warming above- 70 C. After addition was complete, the mixture was stirred at-78 C for an additional 30 minutes. Excess hydride was quenched by the dropwise addition of 20 mL of pre-chilled (-78 C) methanol, again keeping the reaction temperature below- 70 C. The resulting white slurry was poured into 500 mL of ice-cold 1 N HC1. The aqueous layer was extracted with ethyl acetate (3 x 300 mL). The combined organic layers were washed with 300 mL 1 N HC1, and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to yield (S)-4- formyl-2,2-dimethyl-3-oxazolidinecarboxylic acid tert-butyl ester (14.65 g) as a yellow oil. The residue was dissolved in 200 mL of anhydrous methanol, and the flask was flushed with N2. N-Benzylglycine ethyl ester (23.0 g, 118. 9 mmole) and acetic acid (6. 8 mL, 118. 9 mmole) were added, and the reaction mixture was cooled in an ice bath. A solution of sodium cyanoborohydride in tetrahydrofuran (100 mL, 100 mmole) was added via a cannula under positive N2 pressure. The reaction mixture was stirred at room temperature for 18h. A large excess of solid K2C03 was added until gas evolution ceased. The slurry was concentrated almost to dryness under reduced pressure and the residue was dissolved in 300 mL of dichloromethane. The organic layer was washed with 300 mL of 1: 1: 1 water/saturated NAHC03/BRINE. The aqueous layer was extracted with ethyl acetate (2 x 200 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. Purification of the residue by flash column chromatography (silica gel, gradient: 15% ethyl acetate/hexane to 30% ethyl acetate/hexane) gave 16.83 g (70%) of (S)-4-[(BENZYLETHOXYCARBONYL-METHYLAMINO)- methyl] -2, 2-dimethyl-3-oxazolidinecarboxylic acid tert-butyl ester as a clear viscous oil. MS : 407. 3 (M+1).

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.

Reference£º
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/89915; (2004); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

The molecularity of an elementary reaction is the number of molecules that collide during that step in the mechanism., 497-25-6, If there is only a single reactant molecule in an elementary reaction, that step is designated as unimolecular. 497-25-6, name is Oxazolidin-2-one. A new synthetic method of this compound is introduced below.

497-25-6, General procedure: General nitration procedure.12-14 A steel autoclave (25 cm3) equippedwith sapphire windows containing urethane 1c or amide 3 or 5 (10.0 mmol)was filled with liquid CO2 to 60 bar pressure and cooled to 0 C. ThenN2O5 (2.4 g, 22.0 mmol) solution in liquid CO2 (~ 4 g) cooled to 0-5 Cwas gradually pressed out from an auxiliary high-pressure cell by a freshCO2 flow (2 g min-1) to the reaction autoclave. During the addition, thepressure in the latter raised up to 80 bar. The reaction mixture was stirredat 0-5 C for the time specified in Table 1. Then, CO2 was removed bydecompression and the residue was poured onto ice water (50 ml). Theresulted suspension was extracted with EtOAc (4 ¡Á 20 ml), the combinedorganic extracts were washed successively with saturated aqueous NaHCO3(2 ¡Á 20 ml) and water (25 ml) and dried over anhydrous Na2SO4. Thesolvent was removed under reduced pressure to afford corresponding nitrocompounds 2, 4 (see Table 1). Compounds 2a,b and 7 were synthesizedby similar procedures using 1.2 g (11.0 mmol) or 6.0 g (55 mmol) ofN2O5, respectively.

Any one of these steps may be slow and thus may serve as the rate determining step. In general, however, in the presence of the catalyst, the overall rate of the reaction is faster than it would be if the reactants were in the gas or liquid phase.

Reference£º
Article; Kuchurov, Ilya V.; Fomenkov, Igor V.; Zlotin, Sergei G.; Tartakovsky, Vladimir A.; Mendeleev Communications; vol. 23; 2; (2013); p. 81 – 83;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

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. 875444-08-9, name is (4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one,below Introduce a new synthetic route., 875444-08-9

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.

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. 875444-08-9, if you are interested, you can browse my other articles.

Reference£º
Patent; LEK Pharmaceuticals d.d.; EP2468736; (2012); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem