tert-Butanol → HCID 68692696, compound

Participants

Reaction Steps

A solution of 210 (1.95 g, 4.52 mmol), DPPA (1.49 g, 5.43 mmol) and Et3N (1.01 g, 9.95 mmol) in t-BuOH (40 mL) was heated at reflux for 15 h. The solvents were removed under reduced pressure and the residue purified by chromatography on silica gel, eluting with petroleum ether/EtOAc (4:1), to give tert-butyl 7-[(dibenzylamino)sulfonyl]-2-naphthylcarbamate (211) (1.37 g, 62%). A sample was recrystallised from Et2O/petroleum ether as colorless needles: mp 139-140° C.; 1H NMR (CDCl3) δ8.51 (d, J=1.2 Hz, 1H), 8.03 (d; J=1.3 Hz, 1H), 7.86 (d, J=8.7 Hz, 1H), 7.82 (d, J=8.9 Hz, 1H), 7.68 (dd, J=8.6, 1.8 Hz, 1H), 7.57 (dd, J=8.8, 2.1 Hz, 1H), 7.22-7.12 (m, 6H), 7.08-7.01 (m, 4H), 6.75 (s, 1H), 4.37 (s, 4H), 1.56 (s, 9H); 13C NMR δ 152.1, 137.7, 137.0, 135.1, 132.5, 130.6, 128.5, 128.2, 128.1, 127.9, 127.2, 127.1, 121.3, 120.6, 114.9, 80.6, 50.1, 27.8. Anal. (C29H30N2O4S) C, H, N.

Provenance & Evidence