Tag: 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

A solution of hexyllithium 2.3 M in hexane (18.3 ml, 42.1 mmol) is added at 0 C. and under nitrogen to a solution of diisopropylamine (5.19 ml, 42.1 mmol) in anhydrous tetrahydrofuran (10 ml). After 15 minutes the solution is cooled to -78 C. and a solution of (S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one (compound (XV), 10 g, 38.3 mmol), in THF (5 ml) is added dropwise. After 45 minutes at -78 C., tert-butylbromoacetate (10.7 ml, 72.7 mmol) is added. The temperature is raised to 20 C. in 4 hours, then a saturated solution of ammonium chloride (50 ml) is added, the tetrahydrofuran is evaporated and the suspension thus obtained is extracted twice with ethyl acetate (2*100 ml). The combined organic phases are washed with 0.5N HCl, brine and are dried over sodium sulphate. After evaporating the solvent in a rotary evaporator, 16.48 g of raw product are obtained (orange-coloured solid), which is purified by flash chromatography (8:2 cyclohexane/ethyl acetate), obtaining 6.1 g of product as white solid (yield 50%). Alternatively the product can be purified by crystallizing the raw reaction product from isopropanol. 1H NMR (300 MHz, CDCl3, 298K) delta 7.37-7.20 (m, 5H), 4.70-4.60 (m, 1H), 4.20-4.08 (m, 3H), 3.35-3.25 (dd, J=13.5 Hz, 3.1 Hz.1H), 2.85-2.75 (dd, J=28.9, 10.1 Hz, 1H), 2.75-2.65 (dd, J=13.8, 10.11 Hz, 1H), 2.47-2.37 (dd, J=16.8 Hz, 3.1 Hz, 1H), 2.01-1.91 (m, 1H), 1.45-1.35 (s, 9H).1.05-0.95 (d, J=6.7 Hz, 3H), 0.95-0.85 (d, J=6.7 Hz, 3H). 13C NMR (75 MHz, CDCl3, 298K) delta 176.8, 173.1, 154.4, 137.1, 130.5, 130.2, 178.3, 81.6, 66.9, 57.0, 45.4, 38.5, 34.6, 31.1, 29.2, 21.7, 19.5.

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

Reference£º
Patent; Chemo Iberica, S.A.; Taddei, Maurizio; Russo, Adele; Cini, Elena; Riva, Renata; Rasparini, Marcello; Carcone, Luca; Banfi, Luca; Vitale, Romina; Roseblade, Stephen; Zanotti-Gerosa, Antonio Carlo; US2013/71899; (2013); 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.

Under N2 protection,500mL three flask, compound 4 (26.83g, 102.7mmol) was dissolved In 80mL ofanhydrous THF a low temperature (-50 C) was added dropwise with 1.0M LiHMDS(110mL, 110 mmol), After the addition was complete, -50 C under stirring for1h, and then added dropwise 1,3-dimethyl-3,4,5,6-tetrahydro-2- Pyrimidone(DMPU) (28.95g, 225.8mmol), the addition was complete the mixture was stirredat -50 C under 0.5h After the addition of cis-2-butene-1,4-dibromo-5 (8.78g,41.0mmol) in 18mL anhydrous THF, Stirred for 1h at -50 C, the naturallywarmed to 0 C, kept at 0 C 1h, then rose to 5-10 C insulation 1.5h, TLCplate track points to the end of the reaction. With 50mL of saturated solutionof NH4Cl quench the reaction, Rotary evaporation to remove THF, (30mL ¡Á 3) theaqueous phase was extracted with ethyl acetate, the combined EA phases werewashed with 1M (50mL ¡Á 4) EA dilute HCl rinse with about three times, driedover anhydrous MgSO4, spin-dry, drain the solvent, The crude product wasrecrystallized from methanol. To give a white crystalline solid was 20.72g,namely the title compound 2.3, Yield 88%.

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

Reference£º
Patent; ZHEJIANGHISOAR PHARMACEUTICAL CO., LTD; PAN, XIANHUA; LIU, FENG; LI, HONGMING; HUANG, RUI; LI, YIMING; ZHANG, QUNHUI; DENG, FEI; CHEN, WENBIN; (21 pag.)CN103059012; (2016); B;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem