Category: 145589-03-3

145589-03-3, (R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(iii) A 1.6M solution of butyllithium in hexane (93.9 ml) was added dropwise over 30 minutes to a stirred solution of diisopropylamine (21.9 ml) in dry tetrahydrofuran (THF) (200 ml) at 0 C. under an atmosphere of argon. The temperature was maintained at 0 C. for 30 minutes and then the solution was cooled to -40 C. A solution of (4S)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one (31.3 g) (obtained as described in Tetrahedron. 1987, 44, 5525) in dry THF (70 ml) was added dropwise over 30 minutes. The solution was kept at -40 C. for 30 minutes and then the temperature was allowed to rise to 0 C. A solution of iodide (C) (39.0 g) in dry THF (75 ml) was added dropwise over 30 minutes, and then the solution was stirred at 0 C. for 1 hour. Saturated sodium chloride solution (250 ml) was added and the mixture was extracted with ether (3*250 ml). The extracts were washed with saturated sodium chloride solution (2*250 ml) and dried (MgSO4). The solvent was removed by evaporation and the residue was purified by flash chromatography, eluding with ethyl acetate/hexane (8:92 v/v), to give (4s)-4-benzyl-3-[(2S,4E)-6-cyclohexyl-2-isopropylhex-4-enoyl]oxazolidin-2-one (A) (34.5 g) as a clear oil; NMR: 0.8 -1.2(complex m, 12H), 1.6(m, 6H), 1.85(t, 1H), 2.0(m, 2H), 2.35(m, 2H), 2.6(m, 1H), 3.3(dt, 1H), 3.8(m, 1H), 4.1(d, 1H), 4.7(m, 1H), 5.4(m, 2H), 7.3(m, 5H); mass spectrum (+ve FAB), 398 (M+H+); 22 [alpha]436 +45.8 (c, 1.04, CHCl3).

145589-03-3, The synthetic route of 145589-03-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Imperial Chemical Industries PLC; US5254697; (1993); A;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

145589-03-3, (R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 1 Preparation of cis-2(S),7(S)-diisopropyl-octe-4-enedioic acid (IIb) from VIIIa To a solution of 4(S)-benzyl-3-isovaleroyl-oxazolidin-2-one (12 g, THL 2000, 41, 10085), dissolved in THF (80 ml), under inert atmosphere cooled to -70 C. 1M-solution of lithium hexamethyldisilazide in toluene (LiHMDS, 50 ml) was slowly added dropwise under stirring at -70 C. within a period of ca. 1 hr. After stirring at the same temperature for 1 hr the reaction mixture was wormed to 0 C., then again cooled down to -70 C. and cis-1,4-dibromo-but-2-ene (4.5 g) in THF (10 ml) was slowly added, the reaction mixture shortly stirred at -70 C., then warmed to it and stirred for 7 hrs and finally poured on mixture of ice water and saturated sodium chloride solution (400 ml, 1:1). The aqueous phase was extracted 3 times with ethylacetate (3*200 ml), the combined organic phases washed once with saturated sodium bicarbonate solution (200 ml), dried with sodium sulphate, filtered and the filtrate evaporated under vacuum providing compound (IIa) as cis-2(S),7(S)-diisopropyl-oct-4-enedioic acid [bis((4(S)-benzyl-oxazolidin-2-one)]amide as a single diastereomer: crude 9.2 g (77% isolated yield) as a yellow semi crystalline oil. To stirred solution of the crude compound (IIa) (9.2 g), dissolved in a mixture of THF (100 ml) and water (30 ml), at 0 C. 35% aqueous hydrogen peroxide (30 ml) followed by 5 M aqueous solution of LiOH (70 ml) were added. After stirring for 1 hr at 0 C. the solution was warmed to rt and stirred over night. After addition of 0.5 M aqueous solution of Na2SO3 (70 ml) and water (70 ml) the aqueous phase was washed 3 times with MTBE to recover the chiral auxiliary. The aqueous phase was then acidified with conc.-HCl to pH 1, extracted 3 times with MTBE (3*200 ml), the combined organic phases dried over MgSO4, filtered and the filtrate concentrated under reduced pressure providing the title compound (IIb) (cis-2(S),7(S)-2,7-diisopropyloct-4-enedioic acid) as a single diastereomer as white crystals crude 3.9 g (95% isolated yield): Anal. calculated for C14H24O4: C, 65.60; H, 9.44; O 24.97. Found: C, 65.53; H, 9.38; O 24.88., 145589-03-3

145589-03-3 (R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one 11391340, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; CarboDesign LLC; US2011/137047; (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.145589-03-3,(R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one,as a common compound, the synthetic route is as follows.

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

145589-03-3 (R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one 11391340, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/6532; (2007); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

145589-03-3, (R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Eine Loesung von 290 g 4S-Benzyl-3-(3-methyl-butyryl)-oxazolidin-2-one in 0,58 l Tetrahydrofuran wird auf -78 C gekuehlt und waehrend 65 Minuten 1,14 l 1 M Lithiumhexamethyldisilazid (in Tetrahydrofuran) zugetropft. Das Gemisch wird noch 1 Stunde bei -78 C nachgeruehrt und anschliessend mit der vorbereiteten Loesung von trans-1-Chloro-3-iod-propen in Tetrahydrofuran versetzt. Man laesst die Temperatur auf 0 C steigen und ruehrt noch weitere 20 Stunden nach. Das Reaktionsgemisch wird mit 500 ml 10%-iger Ammoniumchloridloesung versetzt und mit Diethylether extrahiert (2x 1 l). Die organischen Phasen werden mit Wasser (1x 1 l) gewaschen, mit Natriumsulfat getrocknet und eingedampft. Aus dem Rueckstand wird mittels Flashchromatographie (SiO2 60F / Essigsaeureethylester/Hexan 5:1) die Titelverbindung B3 als leicht oranges Oel erhalten (582 g, 78 %). 1H-NMR (400 MHz, CDCl3, delta) : 0,85 (m, 6H), 2,02(m, 1H), 2,3 – 2,55 (m, 2H), 2,75 (m, 1H), 3,30 (m, 1H), 3,88 (m, 1H), 4,18 (m, 2H), 4,70 (m, 1H), 5,80 – 6,10 (m, 2H), 7,15 – 7,40 (m, 5H) ppm. Herstellung von trans- 1-Chlor-3-iod-propen: Eine Loesung von 184,7 g trans-1,3-Dichlorpropen in 0,58 l Tetrahydrofuran wird mit 266,1 g Natriumiodid versetzt und unter Lichtausschluss waehrend 30 Minuten bei Raumtemperatur geruehrt. Das Gemisch wird klarfiltriert und das Filtrat direkt eingesetzt., 145589-03-3

As the paragraph descriping shows that 145589-03-3 is playing an increasingly important role.

Reference£º
Patent; Speedel Pharma AG; EP1200384; (2004); B1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.145589-03-3,(R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one,as a common compound, the synthetic route is as follows.

: Preparation of (S)-3-((S)-2-isopropylpent-4-enoyl)-4-benzyloxazolidin-2-one [Show Image] (a) Alkylation with allyl bromide: To a solution of lithium diisopropylamide (23 mL, 46 mmol; 2 M in THF) in anhydrous THF (120 mL), stirred at -78 C under argon, a solution of (S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one (10.0 g, 38.27 mmol) in anhydrous THF (10 mL) was added and the mixture was stirred for 1.5 h. Then allyl bromide (16.22 g, 134.07 mmol) and DMPU (16 mL) were successively added dropwise. The resulting mixture was continued to stir at -78 C for 2 h and then allowed to reach -45 C at which it was stirred for 4 h. The mixture was allowed to warm to 10 C during 12 h. The reaction was quenched by the addition of saturated aqueous NH4Cl solution (100 mL) and the product was extracted with ethyl acetate (3 ¡Á 250 mL). The combined organic layers were successively washed with ice-cold HCl (1 M, 100 mL), saturated aqueous NaHCO3 solution (2 ¡Á 100 mL), and brine (2 ¡Á 100 mL), and then dried over anhydrous Na2SO4. After removal of the solvents under reduced pressure 14.46 g of crude product were obtained which were further purified by radial chromatography on silica gel (petrolether/ethyl acetate = 10:1) to afford 8.994 g (78 %) of alkylation product as a yellowish oil

145589-03-3, 145589-03-3 (R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one 11391340, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; Krka Tovarna Zdravil, D.D., Novo Mesto; EP2189442; (2010); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

145589-03-3, (R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(b) Alkylation with allyl iodide: To a solution of lithium diisopropylamide (23 mL, 46 mmol; 2 M in THF) in anhydrous THF (120 mL), stirred at -78 C under argon, a solution of (S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one (10.0 g, 38.27 mmol) in anhydrous THF (10 mL) was added and the mixture was stirred for 1.5 h. To the resulting mixture allyl iodide (10.30 g, 61.32 mmol) was added dropwise and stirring was continued for another 30 min. The resulting mixture was warmed to -45 C at which it was stirred for 15 h. The reaction was quenched by the addition of 1 M aqueous HCl solution (100 mL) and the product was extracted with ethyl acetate (3 ¡Á 250 mL). The combined organic layers were successively washed with ice-cold 1 M aqueous HCl solution (100 mL), saturated aqueous Na-HCO3 solution (2 ¡Á 100 mL), and brine (2 ¡Á 100 mL), and dried over anhydrous Na2SO4. After removal of the solvents under reduced pressure 11.952 g of crude product were obtained which were further purified by radial chromatography on silica gel (petrolether/ethyl acetate = 10:1) to afford 8.302 g (72%) of alkylation product as a colourless oil. 1H NMR (300 MHz, CDCl3) delta: 0.98 (d, 6H), 1.98 (m, 1H), 2.35-2.54 (m, 2H), 2.64 (dd, 1H), 3.31 (dd, 1H), 3.83-3.90 (sym m, 1H), 4.12-4.17 (m), 4.65-4.73 (m, 1H), 5.02 (d, 1H), 5.09 (ddt 1H), 5.76-5.90 (m, 1H), 7.22-7.36 (m, 5H).

145589-03-3, 145589-03-3 (R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one 11391340, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; Krka Tovarna Zdravil, D.D., Novo Mesto; EP2189442; (2010); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem