Methyl chloroformate → HCID 11951493, compound

Participants

Reaction Conditions

Reaction Steps

Methyl chloroformate (0.022 ml, 0.282 mmol) is added dropwise to (R)-5-(5-aminomethyl-2-oxo-oxazolidin-3-yl)-7-fluoro-1-(2-fluoro-ethyl)-1,3-dihydro-iridol-2-one (0.080 g, 0.188 mmol) and diisopropylethylamine (0.137 ml, 0.752 mmol) in dichloromethane (2 ml) at 0° C. The reaction is stirred at 0° C. for 30 minutes and then allowed to warm at room temperature. The reaction mixture is diluted with dichloromethane, washed with water and brine, dried (Na2SO4) and evaporated. The residue is purified by PTLC (5% MeOH/DCM) to give the title compound as an off white solid. HPLC r.t. 3.93 min; 1H NMR (300 MHz, CDCl3) 7.32 (m, 1H), 7.25 (m, 1H), 5.15 (m, 1H), 4.77 (m, 1H), 4.75 (t, J=5.1 Hz, 1H), 4.57 (t, J=4.8 Hz, 1H), 4.22 (t, J=5.1 Hz, 1H), 4.14 (t, J=4.8 Hz, 1H), 4.02 (t, J=9 Hz, 2H), 3.80 (dd, J=6.6, 9 Hz, 1H), 3.69 (s, 3H), 3.61 (s, 2H), 3.50-3.69 (m, 2H); MS for C16H17F2N3O5 m/z 370.0 (M+H)+.

Provenance & Evidence