Diisopropylethylamine → HCID 74059718, compound

Participants

Reaction Steps

N,N-Diisopropylethylamine (0.507 ml, 2.91 mmol) was added to 3-[4-(diethoxy-phosphoryloxy)phenyl]acrylic acid (0.065 g, 0.217 mmol) [prepared according to the procedure described in Tetrahedron Lett 1996, 37, 3635] and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.124 g 0.326 mmol) in DMF (3 ml) and stirred for 20 minutes at room temperature. 2-[4-(5(S)-aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluorophenyl]-4H-[1,3,4]thiadiazin-5-one (0.084 g, 0.259 mmol) was added and stirring continued at room temperature overnight. The reaction mixture was partially evaporated under vacuum, diluted with water (5 ml), and extracted with ethyl acetate (50 ml). The extract was washed with brine, dried (MgSO4), and evaporated. The residue was purified by PTLC (5% MeOH/DCM) to give pure product as a white solid (0.71 g, 54%); MS (m/z): [M+H]+=607.

Provenance & Evidence