D-Threonine → HCID 86699961, compound

Participants

Reaction Steps

To a stirred mixture of D-threonine (0.146 g, 1.23 mmol) and NaHCO3 (0.155 g, 1.85 mmol) in H2O (3.0 mL), the crude mixture containing 1,3-benzodioxol-5-yl-methyl-2-pyridyl carbonate and 1,3-benzodioxol-5-yl-methyl-2-oxopyridine-1-carboxylate (0.506 g, 1.85 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 (0.337 g, 92%) as transparent oil, which was used in the next step without further purification. MS (ESI) m/z: 315 [M−NH4]+; (ESI) m/z: 296 [M−H]−. 1H NMR (DMSO-d6): δ 1.09 (d, J=6.4 Hz, 3H), 3.95 (dd, J=3.5, 9.0 Hz, 1H), 3.99-4.08 (dq, J=3.5, 6.4 Hz, 1H), 6.01 (s, 2H), 4.95 (s, 2H), 6.78-7.00 (m, 3H).

Provenance & Evidence