Heterocyclic Building Blocks-Oxazolidine

95530-58-8, 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. 95530-58-8, name is (R)-4-Isopropyloxazolidin-2-one. A new synthetic method of this compound is introduced below.

To a solution of (R) -4-isopropyloxazolidin-2-one (25.0g, 0.194mol, 1.0eq) in anhydrous THF (1150 mL) was added n-BuLi (85.0 mL, 0.213mol, 1.1eq) at -78 under N2and the mixture was stirred at the same temperature for 1 h, a large number of white solids formed. Then propionyl chloride (20.0 mL, 0.232mol, 1.2eq) was added at -78 and the mixture was stirred at the same temperature for 1 h. After the consumption of (S) -4-isopropyloxazolidin-2-one monitored by TLC, the solution was poured into saturated ammonium chloride solution (1.2 L) and the mixture was extracted with EA (700 mL, 350 mL ¡Á 2) . The organic extract was washed with 1.0 N NaOH solution (1.0 L) and brine (1.0 L) , dried over anhydrous sodium sulfate, filtered, concentrated in vacuo and purified by SiO2column chromatography (PE : EA = 10: 1) to give the title compound as a colorless oil (32.6 g, 90.8%) . ESI m/z: calcd for C9H17NO3[M+H]+: 186.1, found 186.1.1H NMR (400 MHz, CDCl3) delta 4.48 -4.37 (m, 1H) , 4.27 (t, J = 8.7 Hz, 1H) , 4.21 (dd, J = 9.1, 3.1 Hz, 1H) , 3.04 -2.82 (m, 2H) , 2.45 -2.30 (m, 1H) , 1.17 (t, J = 7.4 Hz, 3H) , 0.90 (dd, J = 17.1, 7.0 Hz, 6H) .

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; HANGZHOU DAC BIOTECH CO. LTD; ZHAO, Robert Yongxin; YANG, Qingliang; HUANG, Yuanyuan; ZHAO, Linyao; GAI, Shun; YE, Hangbo; LEI, Jun; XU, Yifang; CAO, Mingjun; GUO, Huihui; JIA, Junxiang; TONG, Qianqian; LI, Wenjun; ZHOU, Xiaomai; XIE, Hongsheng; BAI, Lu; CAI, Xiang; ZHUO, Xiaotao; ZHANG, Xiuzheng; ZHENG, Jun; (424 pag.)WO2019/127607; (2019); 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., 2346-26-1, If there is only a single reactant molecule in an elementary reaction, that step is designated as unimolecular. 2346-26-1, name is Oxazolidine-2,4-dione. A new synthetic method of this compound is introduced below.

2.2. 1,1-dimethylethyl 4-[(2,4-dioxo-1,3-oxazolidin-3-yl)methyl]piperidine-1-carboxylate A suspension of 13.60 g (46.36 mmol) of 1,1-dimethylethyl 4-{[(methylsulphonyl)oxy]methyl}piperidine-1-carboxylate, prepared in step 2.1., 9.37 g (92.72 mmol) of 1,3-oxazolidine-2,4-dione and 16.02 g (139.08 mmol) of 1,1,3,3-tetramethylguanidine in a mixture of 180 ml of tetrahydrofuran and 30 ml of dimethylformamide is heated at reflux for 24 hours. It is allowed to return to ambient temperature and is concentrated under reduced pressure. The residue is taken up in dichloromethane and water and the aqueous phase is separated off and extracted twice with dichloromethane. The combined organic phases are washed with saturated aqueous sodium chloride solution and dried over sodium sulphate. Following evaporation of the solvent, the residue obtained is purified by chromatography on silica gel, eluding with a 98/2 then 95/5 mixture of dichloromethane and methanol. This gives 12.53 g of product in the form of an orange-brown solid., 2346-26-1

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; SANOFI-AVENTIS; US2007/21403; (2007); A1;,
Oxazolidine – Wikipedia
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17016-83-0, 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. 17016-83-0, name is (S)-4-Isopropyl-2-oxazolidinone, introduce a new downstream synthesis route as follows.

Preparation 8 According to the literature (Kruse et AL., J. Med. Chem. (1987), 30,486-494), a solution of 3, 5-difluorocinnamic acid (9.94 g, 53.9 mmol) in THF (100 ML) was hydrogenated over 10% Pd/C (1.50 g) at 50 psi of H2 pressure for 5 h at RT. The mixture was filtered and concentrated under reduced pressure to yield the 3- (3, 5- difluoro-phenyl) propionic acid (10.9 g, 100%). Oxalyl chloride (13 ml, 150 mmol) was slowly added to a solution of the acid (10.9 g, 53.9 mmol) in THF (220 ML) at 23 C, followed by the addition of a catalytic amount of DMF (1 drop). After 90 min at RT, the volatiles were removed under reduced pressure and the resulting residue was twice coevaporated with dry benzene to yield 3- (3, 5-DIFLUOROPHENYL)-PROPIONYL CHLORIDE as a yellow oil (11.91 g, 100%). The acid chloride was used in the ensuing step without further purification. The acylation was carried out in analogy to the literature (Pettit et al. Synthesis (1996), 719-725). A solution of (S)- (-)-4-ISOPROPYL-2- oxazolidinone (6.46 g, 50 mmol) in THF (150 ML) was stirred under argon and cooled to-78 C. n-BuLi (2.45 M in hexanes, 20.8 ML, 50.96 mmol) was added dropwise, followed by a solution of the previously prepared 3- (3, 5-DIFLUOROPHENYL)-PROPIONYL chloride in THF (8 ML). After warming the reaction to 23 GC over 15 h, the reaction was quenched with saturated aq. NH4CI (30 ml), followed by removal of the volatiles in vacuo. The slurry was extracted with CH2CI2 (2x), and the combined organic layers washed with 1 M NAOH (2x) and brine, dried (NA2SO4) and concentrated in vacuo. Purification of the residue by chromatography over SILICA GEL (15O30% EtOAc/hexanes) gave the product (14.27 g, 48 mmol, 96%). 1H NMR (400 MHz, CECI3) 8 6. 73 (m, 2 H), 6.59 (m, 1 H), 4.37 (m, 1 H), 4.17-4. 25 (m, 2 H), 3.24 (m, 1 H), 3.16 (m, 1 H), 2.93 (m, 2 H), 2.30 (m, 1 H), 0.86 (d, 3 H, J= 6.8 Hz), 0.80 (d, 3 H, J= 6.8 Hz); LCMS (Conditions A): tR = 4.47 min: 595 (2M+H) +, 298 (M+H) +.

A chemical reaction often occurs in steps, although it may not always be obvious to an observer. Thank you very much for taking the time to read this article. If you are also interested in other aspects of 17016-83-0, you can also browse my other articles.

Reference£º
Patent; SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC; WO2005/16876; (2005); A2;,
Oxazolidine – Wikipedia
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497-25-6, 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. 497-25-6, name is Oxazolidin-2-one. A new synthetic method of this compound is introduced below.

Example 101 (R) and (S) -3- (5′-fluoro-2,2-dimethyl-2′-oxospiro [cyclopropane- 1 ,3′-hidoline] – 1 ‘-yl) -5- (2-oxooxazolidin-3-yl)benzoic acidSynthesis of methyl-3-bromo-5-(2-oxooxazolidin-3-yl)benzoateA suspension of 3-bromo-5-iodo-benzoic acid methyl ester (682 mg, 2 mmol), oxazolidin- 2-one (191 mg, 2.2 mmol), Cul (76 mg, 0.4 mmol), potassium carbonate (545mg, 4mmol) and N, N’-dimethyl-ethane-l,2-diamine (86uL, 0.8mmol) in acetonitrile (15 mL) was stirred for 16 hours at 90C. The precipitate was filtered off and washed with ethyl acetate. The filtrate was concentrated in vacuo to afford 3-bromo-5-(2-oxo-oxazolidin-3-yl)- benzoic acid methyl ester (480 mg, 80%) which was used for next step without further purification.

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; F. HOFFMANN-LA ROCHE AG; CHEN, Li; FENG, Lichun; HE, Yun; HUANG, Mengwei; YUN, Hongying; WO2011/70039; (2011); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

2346-26-1, 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. 2346-26-1, name is Oxazolidine-2,4-dione. A new synthetic method of this compound is introduced below.

(3R) -4,4-Dimethyl-2-oxotetrahydrofuran-3-yl (7S) -3-chloro- 2-chloromethyl-5,6,7,8-tetrahydro-4-(4- methoxyphenyl)[1]benzothieno[2,3-b]pyridine-7-carboxylate (0.85 g) obtained in Reference Example 17,2,4-dioxo-1,3-oxazolidine (176.8 mg) and potassium carbonate (263.8 mg) were suspended in DMF (4.25 ml), and the suspension was stirred at the internal temperature of 80 to 85C for 2 hrs. The suspension was cooled to room temperature. Ethyl acetate (17 ml) and water (8.5 ml) were added, and the organic layer was separated and washed with water and 10% brine. The solvent was removed by evaporation to give the title compound as a yellow oil (1.22 g). The product was used in the next step without purification. ?H-NMR (300 MHz, CDC13) 8; 1.08 (3H, s) , 1.18 (3H, s) , 1.73-1.76 (lH, m), 1.93-2.07 (3H, m), 2.90-2.95 (lH, m), 3.14 (2H, d, J=7.3 Hz) , 3.89 (3H, s) , 4.03-4.06 (2H, m) , 4.93 (2H, s) , 5.05 (2H, s) , 5.35 (lH, s), 6.98-7.01 (2H, m), 7.09-7.19 (2H, m)., 2346-26-1

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/111046; (2005); A1;,
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. 2346-26-1, name is Oxazolidine-2,4-dione,below Introduce a new synthetic route., 2346-26-1

EXAMPLE 23; 4-r4-(2,4-Dioxo-oxazolidin-5-ylidenemethyl)-2-methoxy-phenoxy1-naphthalene-1- carbon itrileTo a mixture of oxazolidine-2,4-dione (50.5 mg, 0.50 mmol), LiCI (128 mg, 3.0 mmol) and anhydrous THF (5.0 mL) cooled to -78 0C was added dropwise 1.7 M tert-butyllithium solution in pentane (0.616 mL, 1.05 mmol). After stirring at -78 0C for 20 minutes, the reaction mixture was warmed to 0 0C for 5 minutes. The mixture was recooled to -78 0C and a solution of 4-(4-formyl-2-methoxy-phenoxy)-naphthalene-1 – carbonitrile (Example 19a) was added dropwise. After stirring at -78 0C for 15 minutes, 1 N HCI (1.05 ml_, 1.05 mol) was added dropwise. The reaction mixture was allowed to warm up to room temperature. After evaporation of most of the solvent, p- toluenesulfonic acid monohydrate (85 mg, 0.5 mmol) and toluene (25 ml_) were added. The mixture was heated to reflux with a Dean-Stark trap for 5 hours. After removal of solvent, the residue was taken up with a mixture of DMF and methanol and purified on a preparative HPLC [Waters XTerra Prep MS C8 OBD Column (5 mum, 30 x 50 mm) using a gradient mixture of 0.1 % aqueous TFA and acetonitrile]. 1H NMR (400 Hz, DMSO-c/e) delta 12.45 (s, 1 H), 8.43 (d, 1 H), 8.16 (s, 1 H), 8.11 (d, 1 H), 8.00 (d, 1 H), 7.88 (t, 1 H), 7.77 (t, 1 H), 7.65 (d, 1 H), 7.32 (d, 1 H), 7.09 (s, 1 H), 6.63 (d, 1 H), 3.73 (s, 3H); LC/MS (m/z) [M+1]+ 386.9 (calculated for C22Hi4N2O5, 386.1 )., 2346-26-1

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; JANSSEN PHARMACEUTICA N.V.; WO2008/109727; (2008); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

#REF!

To a solution of 5.6 g of N-isovaleroyl-(S)-4-benzyl-oxazolidin-2-one in 12 ml of toluene are added, at 00C, first of all 23.5 ml of a 1 -molar solution of bis-trimethylsilyl-lithium amide in tetrahydrofuran, then 5.7 g of dimethylpropylene urea. The solution obtained is added dropwise at 00C to a solution of 6 g of trans -1 ,4-dibromobut-2-ene in 10 ml of toluene. After stirring, the mixture is acidified with diluted hydrochloric acid, separated, and the organic solution concentrated. The crude product is purified by chromatography on a column of silica gel (eluant: hexane/ethyl acetate 85:15)., 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; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/6532; (2007); A1;,
Oxazolidine – Wikipedia
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An elementary termolecular reaction involves the simultaneous collision of three atoms, molecules, or ions.(S)-4-Phenyloxazolidin-2-one, cas is 99395-88-7. Here is a downstream synthesis route of the compound 99395-88-7. 99395-88-7

To a precooled (0 C) solution of (S)-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 (S)-4-phenyloxazolidin-2-one (2.03 g, 12.4 mmol) in THF (10.0 mL) was added ra-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 (Na2S04), 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 product (3.20 g, 65%) as white solid. MS: m/z = 437 (M+H+)., 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; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD; WILLIAMS, Peter D.; MCCAULEY, John A.; BENNETT, David Jonathan; BUNGARD, Christopher J.; CHANG, Lehua; CHU, Xin-Jie; DWYER, Michael P.; HOLLOWAY, M. Katharine; KEERTIKAR, Kartik M.; LOUGHRAN, H. Marie; MANIKOWSKI, Jesse J.; MORRIELLO, Gregori J.; SHEN, Dong-Ming; SHERER, Edward C.; SCHULZ, Jurgen; WADDELL, Sherman Tim; WISCOUNT, Catherine M.; ZORN, Nicolas; TUMMANAPALLI, Satyanarayana; SIVALENKA, Vijayasaradhi; HU, Bin; JI, Tao; ZHONG, Bin; WO2015/13835; (2015); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

7517-99-9, 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. 7517-99-9, name is 5-(Hydroxymethyl)oxazolidin-2-one. A new synthetic method of this compound is introduced below.

7517-99-9, Compound 5-(hydroxymethyl)oxazolidin-2-one 23a (2.34 g, 20.0 mmol),Imidazole (1.7 g, 25 mmol) was dissolved in acetonitrile (30 mL).Ice bath to 0 C, then tert-butyldimethylsilyl chloride (3.3 g, 22.0 mmol) was added.The reaction was stirred at 0 C for 0.5 hours and then warmed to room temperature overnight.Adding saturated ammonium chloride solution and ethyl acetate, extracting, and washing the organic phase with saturated ammonium chloride solution three times, dried over anhydrous sodium sulfate, filtered and concentrated,Purification by column chromatography gave the title compound 25a (3.7 g,The yield was 80%.

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; Shanghai Huahuituo Pharmaceutical Technology Co., Ltd.; Zhejiang Huahai Pharmaceutical Co., Ltd.; Xu Xin; Zhang Tian; Li Yunfei; Wang Guan; Zhu Weibo; Li Dongsheng; Qin Chenggang; Liu Chuanduo; Liu Lei; Wu Qimei; Yang Xuqin; Jia Jie; Wang Ying; Chen Yuhao; Wang Yijin; Ge Jian; (143 pag.)CN109897011; (2019); A;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

875444-08-9, 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. 875444-08-9, name is (4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one. A new synthetic method of this compound is introduced below.

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) (280 mg) prepared by procedure of WO 2007/005572 is dissolved in DMF (30 mL) and cooled to -15C. 2 M NaHMDS (3.90 mL, 1.05 eq) was then added over 1 h, followed by addition of the biaryl chloride EBFCI (270 mg) in DMF (5 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 (3.5 mL) was added, followed by 20 mL of 10% IPAC/Heptanes and 40 mL of water, keeping the temperature between 10C and 20C throughout. The layers were cut and the organic layer was washed twice with 20 mL of 1/1 DMF/water followed by two 15 mL water washes. The organic layer was then removed under reduced pressure and the resulting residue was purified by flash chromatography (EtOActhexanes) to remove the excess oxazolidinone (compound of formula XV). The pure (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-3-((5′-ethyl-4′-fluoro-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl)methyl)-4-methyloxazolidin-2-one (DMAP, compound of formula XII”) was obtained as a colorless oil (388 mg, 80%).

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