Tag: 90319-52-1

90319-52-1, (R)-4-Phenyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of methyl fumarate (29) (2.66 g, 20.4 mmol) and pivaloyl chloride (2.70 g, 2.76 mL, 22.5 mmol) in THF (40 mL) was cooled to -20 ¡ãC. Triethylamine (4.13 g, 5.68 mL, 40.8 mmol) was added dropwise, and the mixture was stirred 1.5 h at -20 ¡ãC. The cooling bath was removed, and the solution was allowed to warm to room temperature. Solid LiCl (0.953 g, 22.5 mmol) and (R)-phenyl-oxazolidone 13 (5.00 g, 30.6 mmol) were added portionwise, and the reaction was stirred 12 h H2O (10 mL) and ethyl acetate (50 mL) were added. The layers were separated, and the aqueous layer was extracted with ethyl acetate (2*10 mL). The combined organic layers were washed with 1 M HCl (1*25 mL), saturated Na2CO3 (2*50 mL), saturated brine (1*50 mL), dried (Na2SO4), and concentrated under reduced pressure. The crude product was purified by flash chromatography, eluting with hexanes/ethyl acetate (3:1) to provide 4.38 g (78percent) of the chiral methyl fumarate 30 as a white solid: mp 92-94 ¡ãC; 1H NMR (400 MHz) delta 8.17 (d, J=15.7 Hz, 1H), 7.43 (comp, 5H), 6.87 (d, J=15.7, 1H), 5.50 (dd, J=4.0, 8.9 Hz, 1H), 4.76 (t, J=8.9 Hz, 1H), 4.36 (dd, J=4.0, 8.9 Hz, 1H), 3.81 (s, 3H); 13C NMR (100 MHz) delta 165.1, 163.1, 153.2, 138.2, 133.8, 132.2, 129.1, 128.8, 125.9, 70.2, 57.7, 52.2; IR (neat) 1780, 1727, 1690, 1387, 1341, 1306, 1279, 1196 cm-1; mass spectrum (CI) m/z 275.0869 [C14H13NO5 (M+1) requires 275.0794].

90319-52-1 (R)-4-Phenyloxazolidin-2-one 730425, aoxazolidine compound, is more and more widely used in various.

Reference£º
Article; Hethcox, J. Caleb; Shanahan, Charles S.; Martin, Stephen F.; Tetrahedron; vol. 71; 37; (2015); p. 6361 – 6368;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.90319-52-1,(R)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

Pivaloyl chloride (0.572 g, 4.74 mmol) was added dropwise to a solution of acid 12 (0.500 g, 4.31 mmol) in THF (15mL) at ?20¡ãC. After 1h, 4-(R)-phenyloxazolidinone (13) (2.06g, 12.6 mmol) and LiCl (0.201 g, 4.74 mmol) were added in one portion, and the reaction was warmed to room temperature and stirred overnight. The reaction was diluted with H2O (5mL) and extracted with EtOAc (3¡Á10mL). The combined organic layers were washed with satd aq NaHCO3 (2¡Á5mL), brine (1¡Á5mL), dried (Na2SO3), and concentrated under reduced pressure. The residue was purified via flash column chromatography eluting with hexanes/EtOAc (1:1) to give 0.983 g (87percent) of 14 as a white solid: mp=70?71¡ãC; 1H NMR (CDCl3, 300MHz) delta 7.49 (ddd, J=15.4, 2.0, 2.0Hz, 1H), 7.35 (comp, 5H), 7.07 (ddd, J=15.6, 4.4, 4.4Hz, 1H), 5.51 (dd, J=8.7, 4.1Hz, 1H), 4.73 (dd, J=8.7, 8.7Hz, 1H), 4.30 (dd, J=8.7, 3.8Hz, 1H), 4.14 (dd, J=4.6, 2.0Hz, 2H), 3.42 (s, 3H); 13C NMR (CDCl3, 300MHz) delta 164.4, 153.8, 146.8, 139.3, 129.3, 128.8, 126.2, 120.4, 71.6, 70.2, 58.9, 57.9; MS (CI) m/z 261 [C14H15NO4 (M) requires 261].

The synthetic route of 90319-52-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Hethcox, J. Caleb; Shanahan, Charles S.; Martin, Stephen F.; Tetrahedron; vol. 71; 37; (2015); p. 6361 – 6368;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.90319-52-1,(R)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

Step A: Preparation of (R)-3-cinnamoyl-4-phenyloxazolidin-2-one: A THF (50 mL) solution of (R)-4-phenyloxazolidin-2-one (5.90 g, 36.2 mmol) was cooled to -78 ¡ãC and treated with lithium bis(trimethylsilyl)amide (36.9 mE, 36.9 mmol, 1.0 M in THF) dropwise over 15 minutes. After 15-minute stirring at -78 ¡ãC, a TFTF (10 mL) solution of cinnamoyl chloride (6.33 g, 38.0 mmol) was then introduced. The mixture was stirred for 1 hour at -78 ¡ãC and 2 hours at ambient temperature before it was quenched with saturated NaHCO3 (50 mL) and stirred for 1 hour. The mixture was diluted with EtOAc (200 mL), washed with water and brine, dried over MgSO4, filtered and concentrated to give the product as a pale yellow solid (10.6 g, 99.9percent yield). MS (apci) mlz = 293.9 (M+H).

The synthetic route of 90319-52-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BRANDHUBER, Barbara, J.; KERCHER, Timothy; KOLAKOWSKI, Gabrielle, R.; WINSKI, Sharon, L.; WO2014/78323; (2014); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem