Hydrochloric Acid → HCID 59627130, compound

Participants

Reaction Steps

(3S)-3-Amino-1-hydroxy-6-phenoxy-3,4-dihydro-1,8-naphthyridin-2(1H-one (67) tert-Butyl {(3S)-1-[(tert-butoxycarbonyl)oxy]-2-oxo-6-phenoxy-1,2,3,4-tetrahydro-1,8-naphthyridin-3-yl}carbamate (66) (240 mg, 0.509 mmol) was treated with a solution of HCl in Et2O (2 M, 2 mL) and allowed to stir at RT for 66 h. The solvent was removed under reduced pressure, and the residue was dissolved in a solution of 1:4 (1:9 NH4OH: CH3OH): dichloromethane (0.5 mL). This solution was subjected to silica gel chromatography (Eluant: 1:4 (1:9 NH4OH: CH3OH): dichloromethane) to provide the product as a white solid (83 mg, 61%). LCMS m/z 272.0 (M+1). 1H NMR (400 MHz, CD3OD) δ 2.98 (br dd, J=15, 14 Hz, 1H), 3.18 (dd, J=15.3, 6.2 Hz, 1H), 4.01 (dd, J=13.8, 6.1 Hz, 1H), 7.03-7.07 (m, 2H), 7.17 (br t, J=7.4 Hz, 1H), 7.40 (dd, J=8.5, 7.5 Hz, 2H), 7.44-7.46 (m, 1H), 8.00 (br d, J=2 Hz, 1H).

Provenance & Evidence