Methanol → HCID 86667779, compound

Participants

Reaction Steps

Methyl 4-[(1-azido-3-trifluoroacetamidopropoxy)methyl]benzoate (220 mg; 0.61 mmol) was added to methanol (2.3 mL) and a solution of potassium carbonate (200 mg; 1.4 mmol) in H2O (1.1 mL). The mixture was vigorously stirred at room temperature for 3 h, diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtrated and evaporated. The residue was purified by silica column chromatography (DCM:MeCN 1:1+5% MeOH+1% TEA) to provide methyl 4-[(3-amino-1-azidopropoxy)methyl]benzoate as a liquid in a yield of 110 mg (68%). 1H-NMR (500 MHz, CDCl3): δ=1.78-2.02 ppm (m, 2H), 2.85 ppm (t, J=7.0 Hz, 2H), 3.91 ppm (s, 3H), 4.60 ppm (t, J=6.5 Hz, 1H), 4.62 ppm (d, J=12.5 Hz, 1H), 4.87 ppm (d, J=12.5 Hz, 1H); 13C-NMR (500 MHz, CDCl3): δ=37.79 (in [D6]DMSO this peak splits in two distinct signals with δ=37.92 ppm and 38.93 ppm), 52.21, 70.16, 90.40, 127.55, 129.80, 129.89, 142.17, 166.84 ppm. HRMS [+Scan]; calculated m/z for C12H17N4O3 265.1295; observed mass: 265.1292.

Provenance & Evidence