D-Threonine → HCID 86699950, compound

Participants

Reaction Steps

To a stirred mixture of D-threonine (0.150 g, 1.25 mmol) and NaHCO3 (0.158 g, 1.89 mmol) in H2O (3.5 mL), the crude mixture containing hexyl-2-pyridyl-carbonate and hexyl-2-oxopyridine-1-carboxylate (0.45 g, 1.89 mmol) in THF (3.5 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 (0.27 g, 88%) as transparent oil, which was used in the next step without further purification. 1H NMR (DMSO-d6) δ 0.83-0.90 (m, 3H), 1.08 (d, J=6.3 Hz, 3H), 1.21-1.36 (m, 6H), 1.49-1.59 (m, 2H), 3.89-3.99 (m, 3H), 4.01-4.11 (m, 1H), 6.67 (d, J=9.0 Hz, 1H), 12.30 (br s, 1H).

Provenance & Evidence