Day: September 24, 2020

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).

147959-19-1, 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 fields.

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

95715-86-9, Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,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.

95715-86-9 Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate 688220, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; MEDIVIR AB; WO2008/107365; (2008); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

2346-26-1, Oxazolidine-2,4-dione is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2346-26-1, A mixture of the compound (2.4 g) obtained in Reference Example 3, oxazolidine-2,4-dione (808 mg), potassium carbonate (1.1 g) and N, N-dimethylformamide (DMF, 40 ml) was stirred under heating at 80C for 2 hrs. The reaction mixture was poured into water (100 ml), and extracted with ethyl acetate. The extract layer of ethyl acetate was washed with water and saturated brine and dried over magnesium sulfate. The solvent was removed by evaporation under reduced pressure to give the title compound as colorless crystals (2.2 g, 81%), which were recrystallized from ethyl acetate-hexane. Melting point: 118-119C. ?H-NMR (CDC13) 8; 1.24 (3H, t, J=7.4 Hz) , 1.58-1.77 (lH, m) , 1.84-2.07 (3H, m), 2.60-2.80 (lH, m), 3.00-3.10 (2H, m), 3.90 (3H, s) , 4.14 (2H, q, J=7.4 Hz) , 4.93 (2H, s) , 5.06 (2H, s) , 6.95-7.06 (2H, m), 7.07-7.23 (2H, m).

As the paragraph descriping shows that 2346-26-1 is playing an increasingly important role.

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/111046; (2005); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

17016-83-0, (S)-4-Isopropyl-2-oxazolidinone is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Butyllithium (2.5 M in hexane, 15.6 mL, 39.1 mmol, 1.01 equiv) was added dropwise to a solution of (S)-(+)-4-isopropyl-1,3-oxazolidin-2-one2 (5.00 g, 38.7 mmol) in anhydrous THF (70.0 mL) at -78 C under argon. The resulting mixture was stirred for 15 min and a freshly distilled 2-methyl-2E-pentenoyl chloride (5.13 g, 38.7 mmol) in dry THF (30 mL) was added via syringe at -78 C. The reaction was stirred for an additional 45 min at -78 C and then warmed to ambient temperature. Saturated aqueous ammonium chloride (50 mL) was added and the resulting mixture stirred for 30 min. The solvent was removed under reduced pressure and the remaining aqueous phase transferred to a separation funnel. The aqueous phase was extracted with DCM (2¡Á100 mL), the combined organics were washed with 3.0 M NaOH (25 mL), water (25 mL), brine (25 mL), dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified with flash chromatography using hexanes/ethyl acetate 0-20% as a gradient to give 96% (8.37 g) of A as a white solid., 17016-83-0

17016-83-0 (S)-4-Isopropyl-2-oxazolidinone 7157133, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Article; Banasik, Brent A.; Wang, Lee; Kanner, Arielle; Mikael Bergdahl; Tetrahedron; vol. 72; 19; (2016); p. 2481 – 2490;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

875444-08-9,875444-08-9, (4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of (45,5J?)-5-[3;5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (12.00 g, 38.3 mmol) in THF (200 mL) was cooled to 0 C. NaH (0.919 g, 38.3 mmol) was added. The mixture was stirred at 0 C for 30 min. The title compound from Step A (10.0 g, 31.9 mmol) in THF (30 mL) was added. The mixture was stirred at 0 C and then room temperature for 4 h. Saturated NH C1 (10 mL) was added. The mixture was extracted with ethyl acetate (3 xlOO mL). The combined organic fractions were washed with brine (saturated, 20 mL), dried (Na2S0 ), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 65i, eluting with EtOAc/hexane (20/80) to give the title compound as a colorless solid. NMR (CDCl3s 500 MHz) delta 8.57 (s, 1H), 7.94 (s, 1H), 7.82 (s, 2H), 5.86 (d, J= 8.5 Hz, 1H), 4.97 (d, J- 18.0 Hz, 1H), 4.46 (m5 1H), 4.28 (d, J= 17.5 Hz, 1H), 2.60 (s, 3H), 0.83 (d, J= 6.5 Hz 3H)

As the paragraph descriping shows that 875444-08-9 is playing an increasingly important role.

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.17016-83-0,(S)-4-Isopropyl-2-oxazolidinone,as a common compound, the synthetic route is as follows.

[0351] Method A: nBuLi (1.6 M in hexanes, 7.6 ml, 12.2 mmol, 1.5 eq) was added slowly to a stirred solution of (S)-4-isopropyloxazolidin-2-one (Aldrich, 1.5 g, 11.6 mmol, 1 eq) in 20 ml anhydrous THF at -78 C. After 10 min 3-phenylpropanoyl chloride (Aldrich, 1.9 ml, 2.15 g, 12.8 mmol, 1.1 eq) was added dropwise. The reaction was warmed to 0 C. After 1 h the reaction was quenched with saturated aqueous NH4C1. The reaction was stirred at 0 C to room temperature overnight. The reaction was partitioned between water/EtOAc, and the layers were separated. The organic layer was washed with water (x2), brine (xl), and dried over Na2S04. The inorganics were filtered off, and the solvent was removed via rotary evaporation. Purification via flash chromatography on silica gel yielded 2.73 g (10.44 mmol, 90% yield) of (S)-4-isopropyl-3-(3-phenylpropanoyl)oxazolidin-2-one., 17016-83-0

17016-83-0 (S)-4-Isopropyl-2-oxazolidinone 7157133, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; COMENTIS, INC.; BILCER, Geoffrey, M.; LILLY, John, C.; SWANSON, Lisa, M.; WO2011/130383; (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.131685-53-5,(R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone,as a common compound, the synthetic route is as follows.

General procedure: To a solution of imide 11 (548 mg, 2.35 mmol) in CH2Cl2 (11.8 mL) was added dropwise a solution of TiCl4 in CH2Cl2 (1.00M, 3.53 mL, 3.53 mmol) at 0 C. The color of the solution turned to yellow soon. After stirring for 5 min, TMEDA (0.928 mL, 6.23 mmol) was added dropwise. The resulting dark red solution was stirred for 1 h at 0 C before n-octanal (12,0.819 mL, 5.24mmol) was added dropwise. After the resulting mixture was stirred for another 2 h at 0 C, the reaction was quenched with aqueous NH4Cl. The resulting yellow precipitates were filtered off. The filtrate was extracted threetimes with CH2Cl2. The combined organic phases were dried over Na2SO4 and concentrated under reduced pressure.The crude product was purified by silica gel column chromatography (diethyl ether / n-hexane 1:3 to 1:1) to give 13(575 mg, 1.59 mmol, 68%) as a pale yellow oil.

131685-53-5, As the paragraph descriping shows that 131685-53-5 is playing an increasingly important role.

Reference£º
Article; Nakajima, Daisuke; Sueyoshi, Kosuke; Orihara, Kensuke; Teruya, Toshiaki; Yokoshima, Satoshi; Synlett; vol. 30; 8; (2019); p. 924 – 927;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

139009-66-8, (S)-N-Boc-2,2-dimethyloxazolidine-4-carboxylic Acid is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of (4S)-3-(tert-butoxycarbonyl)-2,2-dimethyl-l,3-oxazolidine-4- carboxylic acid (0.56 g, 2.3 mmol) in dry JV,iV-dimethylacetamide (10 mL) was added HATU (0.11 g, 2.87 mmol) and DIEA (0.742 g, 5.75 mmol). After the reaction solution was stirred at rt for 1 h, 6-(4-aminophenyl)-Lambda^-(4-{[2-(trifluoromethyl)pyridin-4- yl]oxy}phenyl)pyrimidine-2,4-diamine (0.84 g, 1.92 mmol) was added. The solution was stirred for an additional 24 h at rt and separated by preparative HPLC to afford a solid intermediate, which was treated with methanol (10 mL) and concentrated HCl (0.5 mL) for 12 h at rt. The resulting mixture was diluted with DMSO and purified by HPLC to give a solid. The solid was stirred with saturated sodium bicarbonate and EtOAc for 2 h. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated to afford 0.433 g (43%) of pure product. 1H NMR (DMSO-J6) delta 9.34 (s, IH), 8.59 (d, IH), 7.88 (m, 4H), 7.76 (d, 2H), 7.37 (s, IH), 7.16 (m, 3H), 6.45 (s, IH), 6.36 (s, 2H), 4.88 (t, IH), 3.56 (m, 2H), 3.39 (m, IH); MS ES 526 (M+H)+ calcd 526.

139009-66-8, The synthetic route of 139009-66-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/99231; (2006); 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.95715-86-9,Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate,as a common compound, the synthetic route is as follows.

95715-86-9, Step 3: Preparation of (S)-3 -(tert-butoxycarbonyl)-2,2-dimethyloxazolidine-4- carboxylic acid (Intermediate 4) To a solution of (5)-3-tert-butyl-4-methyl 2,2-dimethyloxazolidine-3,4- dicarboxylate (6.75 g, 26.0 mmol) in THF (80 mL) and water (40 mL) was added lithium hydroxide hydrate (1.20 g, 28.6 mmol) at room temperature. The reaction mixture was. stirred for 12 hours at room temperature. After evaporation of volatile solvents, the residue was diluted with EtOAc, neutralized with 2 N aq. HC1, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to obtain the title compound (6.32 g, 99%), which was used for the next reaction without further purification.?H-NMR (400 MHz, CDC13): (two sets of rotamers) 4.40-4.5 1 (m, 1H),4.17-4.28 (m, 1H), 4.11-4.15 (m, 1H), 1.62 and 1.67 (s and s, 3H), 1.51 and 1.54 (s and s, 3H), 1.43 and 1.51 (s and s, 9H).

The synthetic route of 95715-86-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; KAINOS MEDICINE, INC.; OH, Su-Sung; CHOI, Minjeong; WO2015/156601; (2015); A1;,
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

497-25-6, Synthesis of (1R, 2R) and (IS, 2S)-methyl-3-(2-(4-chlorophenyl)-5′-fluoro-2-isopropyl- 2′-oxospiro [cyclopropane- 1 ,3′-indoline] – 1 ‘-yl) -5- (2-oxooxazolidin-3-yl)benzoate3-bromo-5-((lS,2S)-2-(4-chlorophenyl)-5′-fiuoro-2-isopropyl-2′-oxospiro[cyclopropane- l,3′-indoline]-l’-yl)benzoate, 3-bromo-5-((lR,2R)-2-(4-chlorophenyl)-5′-fiuoro-2- isopropyl-2′-oxospiro[cyclopropane-l,3′-indoline]-l’-yl)benzoate (0.545 g, 1 mmol), 2- oxazolidone (0.105 g, 1.2 mmol), Cul (20 mg), and K2C03 (0.276 g, 2 mmol) were placed in a Schlenk tube under Argon atmosphere and dissolved in dry acetonitrile. The N, N’- dimethyl-l,2-ehtanediamine (21 L, 20%equiv) was added into the mixture. The mixture was strirred at 80 C for 14 hours. The solvent was removed in vacuo and the residue was purified by flash column chromatography to give the title compound as white powder (0.40 g, 73%). LC/MS m/e calcd. for C30H26CIFN2O5: 548, observed (M+H)+: 549.5

The synthetic route of 497-25-6 has been constantly updated, and we look forward to future research findings.

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