D-Threonine → HCID 86699945, compound

Participants

Reaction Steps

To a stirred mixture of D-threonine (0.15 g, 1.25 mmol) and NaHCO3 (0.16 g, 1.25 mmol) in H2O (3.0 mL), the crude isomeric mixture containing 2-phenethyloxyethyl-2-pyridyl carbonate and 2-phenethyloxyethyl-2-oxopyridine-1-carboxylate (0.54 g, 1.89 mmol) in THF (3.0 mL) was added. After 15 h at rt, the crude mixture was rotary evaporated to remove the organics and subsequently extracted with Et2O (3×5 mL). The aqueous phase was acidified with 2.0 M HCl solution to pH 2-3 and subsequently extracted with EtOAc (3×10 mL). The organic fraction was dried over Na2SO4, filtered and concentrated to dryness to afford the title compound (0.38 g, 94%) as transparent oil, which was used in the next step without further purification. MS (ESI) m/z: 312 [M−H]+; (ESI) m/z: 310 [M−H]−. 1H NMR (DMSO-d6): δ 1.09 (d, J=6.4 Hz, 3H), 2.81 (t, J=7.1 Hz, 2H), 3.55-3.66 (m, 4H), 3.93 (dd, J=3.4, 8.9 Hz, 1H), 4.00-4.15 (m, 3H), 6.83 (d, J=8.9 Hz, 1H), 7.14-7.32 (m, 5H), 12.20 (s, 1H).

Provenance & Evidence