D-Threonine → HCID 86699956, compound

Participants

Reaction Steps

To a stirred mixture of D-threonine (0.119 g, 1.0 mmol) and NaHCO3 (0.125 g, 1.49 mmol) in H2O (3.0 mL), the crude mixture containing (4-cyclohexylphenyl)-methyl-2-pyridyl carbonate and (4-cyclohexylphenyl)-methyl-2-oxopyridine-1-carboxylate (0.464 g, 1.49 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 (0.32 g, 96%) as transparent oil, which was used in the next step without further purification. MS (ESI) m/z: 353 [M−NH4]+; (ESI) m/z: 334 [M−H]−. 1H NMR (DMSO-d6): δ 1.08 (d, J=6.4 Hz, 3H), 1.07-1.55 (m, 6H), 1.63-1.86 (m, 5H), 3.94 (dq, J=3.6, 9.0 Hz, 1H), 4.07 (dd, J=3.6, 6.4 Hz, 1H), 5.00 (s, 2H), 6.88 (d, J=9.0 Hz, 1H), 7.20 (d, J=7.9 Hz, 2H), 7.27 (d, J=7.95 Hz, 2H), 12.54 (s, 1H).

Provenance & Evidence