Propionic Acid → HCID 10287225, compound

Participants

Reaction Steps

1,3-Dicyclohexylcarbodiimide (0.153 g, 0.740 mmol) is added to a mixture of 2-[4-(5(S)-aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluorophenyl]-4H-[1,3,4]thiadiazin-5-one (0.200 g, 0.617 mmol), N,N-diisopropylethylamine (0.161 ml, 0.927 mmol) and propionic acid (0.051 ml, 0.680 mmol) in DMF (3 ml). The mixture is stirred overnight at room temperature and then partially evaporated under vacuum. The residue is diluted with water (5 ml) and the resulting precipitate is filtered and dried under vacuum. Purification by PTLC (10% MeOH/DCM) gives pure product as a white solid (0.21 g, 90%); 1HNMR (300 MHz, DMSO-d6) δ 0.94 (t, J=7.7 Hz, 3H), 2.08 (q, J=7.7 Hz, 2H), 3.40-3.48 (m, 2H), 3.59 (s, 2H), 3.77 (dd, J=6.0, 9.1 Hz, 1H), 4.14 (t, J=9.1 Hz, 1H), 4.74-4.78 (m, 1H), 7.41 (dd, J=2.2, 8.8 Hz, 1H), 7.52 (dd, J=2.2, 14 Hz, 1H), 7.69 (t, J=8.5 Hz, 1H), 8.16 (t, J=5.8 Hz, 1H), 11.6 (s, 1H); mp 192-3; MS (m/z): [M+H]+=381.

Provenance & Evidence