Dimethylformamide → HCID 58292543, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.500 g, 1.99 mmol) in DMF (20 mL) was added NaH (0.176 g, 4.40 mmol) and the mixture was stirred at 0° C. for 45 minutes. A solution of (3-bromo-propyl)-carbamic acid tert-butyl ester (1.04 g, 4.38 mmol) in DMF (5 mL) was added and the mixture was stirred at room temperature for 18 hours. The reaction mixture was quenched with H2O and extracted with EtOAc (3×50 mL). The organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (33-66% EtOAc/Hexane) to give [6-(3-tert-butoxycarbonylamino-propoxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.325 g, 40%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.00 (s, 1H), 6.87 (br. s., 1H), 6.81 (s, 1H), 5.43 (d, J=7.42 Hz, 1H), 3.97-4.10 (m, 2H), 3.93 (t, J=6.06 Hz, 2H), 2.99-3.08 (m, 3H), 2.23 (s, 3H), 2.14-2.22 (m, 1H), 1.72-1.85 (m, 2H), 1.35 (s, 9H), 1.08-1.19 (m, 3H).

Provenance & Evidence