p-Toluenesulfonic acid → HCID 10998777, compound

Participants

Reaction Steps

(4S)-N-tert-Butyloxycarbonyl4-isopropyl-1,3-oxazolidin-5-one (3) was prepared from N-tert-butyloxycarbonyl-(L)-valine (2.17 g, 10.0 mM) and para-toluenesulfonic acid (30 mg) following general procedure A and obtained as a white solid after crystallisation from chloroform (1.67 g, 73%): [a]D20 +104.9 (c 1, CHCl3); mp 43-45° C.; IR (KBr): 1795, 1705 cm-1 ; 1H NMR (200 MHz, CDCl3): 67 5.55 (br, 1H), 5.10 (d, J=4 Hz, 1H), 4.15 (d, J=4 Hz, 1H), 2.21-2.43 (m, 1H), 1.49 (s, 9H), 1.06 (d, J=7 Hz, 3H), 1.02 (d, J=7 Hz, 3H); 13C NMR (50.3 MHz, CDCl3): d 171.8, 152.6, 81.6, 78.4, 59.9, 31.1, 27.9, 17.9, 17.5; LRMS (NH3): 230 (MH+). Anal. Calcd for C11H19NO4 : C, 57.63; H, 8.35; N, 6.11; found: C, 57.62; H, 8.54; N, 5.93.

Provenance & Evidence