D-Threonine → HCID 86699976, compound

Participants

Reaction Steps

To a stirred mixture of D-threonine (0.08 g, 0.67 mmol) and NaHCO3 (0.084 g, 1.0 mmol) in H2O (3.0 mL), the crude mixture containing (4-cyclohexylphenyl)-methyl-2-pyridyl carbonate and [4-(cyclohexoxy)-phenyl]-methyl-2-oxopyridine-1-carboxylate (0.327 g, 1.0 mmol) in THF (3.0 mL) was added. After 15 h at r.t., 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 (0.214 g, 91%) as transparent oil, which was used in the next step without further purification. MS (ESI) m/z: 369 [M−NH4]+; (ESI) m/z: 350 [M−H]−. 1H NMR (DMSO-d6): δ 1.08 (d, J=6.3 Hz, 3H), 1.21-1.48 (m, 5H), 1.48-1.57 (m, 1H), 1.66-1.74 (m, 2H), 1.87-1.95 (m, 2H), 3.95 (dd, J=3.4, 9.0 Hz, 1H), 4.06 (dq, J=3.4, 6.3 Hz, 1H), 4.29-4.36 (m, 1H), 6.84 (d, J=9.0 Hz, 1H), 6.91 (d, J=8.3 Hz, 2H), 7.27 (d, J=8.3 Hz, 2H).

Provenance & Evidence