Methyl chloroformate → HCID 11951669, compound

Participants

Reaction Conditions

Reaction Steps

Methyl chloroformate (0.070 ml, 0.858 mmol) is added dropwise to (R)-5-(5-aminomethyl-2-oxo-oxazolidin-3-yl)-1-cyclopropylmethyl-7-fluoro-1,3-dihydro-indol-2-one (0.300 g, 0.709 mmol) and diisopropylethylamine (0.37 ml, 2.13 mmol) in dichloromethane (15 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 (10% MeOH/DCM) to give the title compound as an off white solid. HPLC r.t. 4.55 min; 1H NMR (300 MHz, CDCl3) 7.52 (1H), 7.39 (s, H), 7.35 (s, 1H), 4.68-4.66 (m, 1H), 4.09 (t, J=9.0 Hz, 1H), 3.74 (dd, J=9, 6 Hz, 1H), 3.69 (s, 2H), 3.59 (d, J=7.2 Hz, 2H), 3.53 (s, 3H), 3.33 (t, J=5.4 Hz, 2H), 1.26-1.23 (m, 1H), 0.47-0.42 (m, 2H), 0.32-0.29 (m, 2H); MS for C18H20FN3O5 m/z 378.1(M+H)+.

Provenance & Evidence