m-Chloroperbenzoic acid → HCID 10042330, compound

Participants

Reaction Steps

Into a 25-mL single-necked round-bottomed flask equipped with a magnetic stir bar were placed 0.63 g (2.0 mmol) of (2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-phenylaziridine (prepared according to Example 1), 1.04 g (3.0 mmol) 3-chloroperoxybenzoic acid (60%, from Aldrich) and 20 mL chloroform. The reaction mixture was stirred at room temperature for 1 h, washed with 20 mL saturated aqueous Na2S2O3 solution, diluted with 50 mL CH2Cl2, washed with saturated aqueous Na2CO3 solution (2×10 mL) and dried (MgSO4). Filtration and removal of the solvent gave a solid residue which was purified by flash chromatography (ethyl acetate:n-pentane, 2:8) to afford the titled compound (0.62 g, 94%): mp. 85°-87° C.; [α]D20 +18.2° (c 1.0, CHCl3); IR (KBr): 3033.3, 1757.2, 1597.5, 1334.1, 1210.1, 1163.6, 1091.7 cm-1 ; 1H NMR (CDCl3) δ2.44 (s, 3H, CH3), 3.49 (s, 3H, CH3), 3.71 (d, J=7.7 Hz, 1H, CH), 4.12 (d, J=7.6 Hz, 1H, CH), 7.20-7.32 (m, 5H, aromatic), 7.35 (d, J=8.4 Hz, 2H, aromatic), 7.92 (d, J=8.3 Hz, 2H, aromatic); 13C NMR (CDCl3) δ164.5, 145.0, 133.8, 130.9, 129.7, 128.3, 128.0, 127.9, 127.2, 52.3, 45.3, 43.3, 21.6. Anal. Calcd for C17H17NO4S: C, 61.61; H, 5.17. Found: C, 61,43; H, 5.17.

Provenance & Evidence