Triethylamine → HCID 131729733, compound

Participants

Reaction Steps

tert-Butyl [(3S)-1-[(tert-butoxycarbonyl)oxy]-6-(3-cyanophenoxy)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]carbonate (88) Sodium acetate trihydrate (4.9 g, 36.3 mmol) was added to a 0° C. solution of 3-(3-cyanophenoxy)-6-nitro-L-phenylalanine (87) (1.3 g, 3.6 mmol) in THF (50 mL) and MeOH (50 mL). The mixture was stirred until all of the salts dissolved, and tin(II) chloride dihydrate (4.2 g, 18.1 mmol) was added. The reaction suspension was stirred at 0° C. for 6 h. Triethylamine (5.1 mL, 36.3 mmol) and BOC2O (1.9 g, 8.7 mmol) were added and the mixture was allowed to stir for 18 h at RT. The reaction mixture was concentrated in vacuo, and the resulting residue was slurried in EtOAc. Insoluble solids were filtered off and washed with EtOAc, and the combined EtOAc fractions were washed with water and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (Gradient: 0% to 50% EtOAc in heptane) to afford the title compound as a white solid (1.1 g, 61%). LCMS m/z 496.2 (M+1). 1H NMR (400 MHz, CDCl3) δ 1.47 (s, 9H), 1.58 (br s, 9H), 2.98 (br dd, J=14, 14 Hz, 1H), 3.41 (v br d, J=14 Hz, 1H), 4.51-4.60 (m, 1H), 5.59 (br s, 1H), 6.91 (br s, 1H), 6.97 (br dd, J=8.5, 2.6 Hz, 1H), 7.0-7.2 (v br s, 1H), 7.19-7.25 (m, 2H), 7.38-7.47 (m, 2H).

Provenance & Evidence