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.
EXAMPLE 6; Preparation of (S)-ie f-butyl-3-((S)-4-benzyloxazolidin-2-on-3-yl)-carbonyl-4- methyl-pentanoate, compound (XVI) in which Z = terf-butyl.; 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, terf-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 x 100 ml). The combined organic phases are washed with 0.5N HCI, 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.1 H NMR (300 MHz, CDCI3, 298K) delta 7.37-7.20 (m, 5H), 4.70-4.60 (m, 1 H), 4.20- 4.08 (m, 3H), 3.35-3.25 (dd, J = 13.5 Hz, 3.1 Hz.1 H), 2.85-2.75 (dd, J = 28.9, 10.1 Hz, 1 H), 2.75-2.65 (dd, J = 13.8, 10.1 1 Hz, 1 H), 2.47-2.37 (dd, J = 16.8 Hz, 3.1 Hz, 1 H), 2.01 -1 .91 (m, 1 H), 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, CDCI3, 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., 145589-03-3
As the paragraph descriping shows that 145589-03-3 is playing an increasingly important role.
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; WO2011/151442; (2011); A2;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem