With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.152305-23-2,(S)-4-(4-Aminobenzyl)oxazolidin-2-one,as a common compound, the synthetic route is as follows.
Concentrated hydrochloric acid (34.0L, 325.5 mol) was slowly added to a stirred solution of 4-(S)-(4-aminobenzyl)-1,3-oxazolidin-2-one 2 (25.0 kg, 130.2mol) in a mixture of methanol (75.0 L) and water (112.5L) at 5?10 ?C. After stirring for 10 min, a solution of sodium nitrite (11.2 kg, 162.7 mol) in water (75 L) was added slowly to the reaction mixture at 5 to 0?C and the solution was maintained under stirring at the same temperature for 30 min. Meanwhile, in a separate vessel, sodium acetate(42.7 kg, 520.8 mol) was added to a stirred solution of ethyl 2-acetyl-5-(1,3-dioxo-1,3-dihydro-2-isoindolyl) pentanoate (4) (43.3 kg, 136.6 mol) in methanol (437.5 L). After stirring for 1 h at 25?30 ?C the solution was cooled to 0?5 ?C, and the previously prepared diazotized solution was slowly added to this cooled reaction mixture and stirredfor 3 h at room temperature. After the completion of reaction (monitored by thin-layer chromatography, TLC, using ethyl acetate as mobile phase), the reactionmass was extracted three times with dichloromethane (3250 L). The combined dichloromethane layer was washed twice with water (2125 L) and once with brine(125 L). The organic layer was separated and concentrated. The crude residue (containing the hydrazone intermediate) was cyclized to form the indole moiety. Methanol (50 L) and methanolic HCl (15.0percent, 150 mL) were added to the residue. and the solution was refluxed for 6 h. The reaction mass was then cooled to room temperature (25 ?C) and the obtained solid was filtered, washed with methanol (25 L), and dried to furnish the title compound 7. Yield 46.8 kg (78percent); mp 215?220 ?C; 1H NMR: (DMSO-d6, 200 MHz): delta 11.55 (s, 1H), 7.78 (s, 4H), 7.4 (s, 1H), 7.35 (d, 1H, J=8.4 Hz), 7.1 (d, 1H, J=8.4 Hz), 4.25 (q, 2H, J=7.2 Hz), 4.08 (m, 1H), 3.9?3.8 (m, 4H), 3.4?3.3 (m, 2H), 2.9?2.6 (m, 2H), 1.35 (t, 3H, J=7.2 Hz); 13C NMR: (DMSO-d6, 50 MHz): delta 14.2, 23.4, 38.4, 40.9, 51.5, 53.2, 60.4, 68.2, 112.7, 118.9, 119.1, 119.9, 122.9, 123.8, 124.1, 126.7, 127.6, 127.7, 131.6, 134.3, 135.3, 158.7, 161.7, 162.1, 167.7; IR numax cm-1(KBr): 3357 (br), 2940 (br), 1759 (br), 1707, 1544, 1466, 1440, 1396, 1248, 1026 cm-1; MS: m/z 462 (100percent, M1; Et ester).
152305-23-2, 152305-23-2 (S)-4-(4-Aminobenzyl)oxazolidin-2-one 7099156, aoxazolidine compound, is more and more widely used in various.
Reference£º
Article; Vujjini, Satish Kumar; Mothukuri, Vivekananda Reddy; Islam, Aminul; Bandichhor, Rakeshwar; Kagga, Mukkanti; Malakondaiah, Golla China; Synthetic Communications; vol. 43; 24; (2013); p. 3294 – 3306;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem