tert-Butanol → HCID 44549670, compound

Participants

Reaction Steps

A solution of acid 178 (50 mg, 0.22 mmol), DPPA (72 mg, 0.26 mmol) and Et3N (48 mg, 0.48 mmol) in t-BuOH (5 mL) was heated under reflux for 20 h. The solvents were removed under reduced pressure and the residue was purified by chromatography eluting with CH2Cl2/MeOH (49:1) followed by recrystallization (EtOAc/petroleum ether) to give methyl 7-[(tert-butoxycarbonyl)amino]-2-naphthoate (179) (52 mg, 80%) as colorless needles. A sample was recrystallised: mp (CH2Cl2/n-hexane) 181-183° C.; 1H NMR (CDCB) δ 8.52 (br s, 1H), 8.05 (br s, 1H), 7.94 (dd, J=8.5, 1.7 Hz, 1H), 7.79 (d, J=8.7 Hz, 2H), 7.51 (dd, J=8.8, 2.1 Hz, 1H), 6.67 (or s, 1H), 3.97 (s, 3H), 1.56 (s 9H); 13C NMR 167.3, 152.7, 136.6, 133.1, 132.0, 130.4, 128.6, 127.9, 127.8, 123.8, 121.5, 115.6, 80.9, 52.2, 28.3. Anal. (C17H19NO4) C, H, N.

Provenance & Evidence