D-Threonine → HCID 86699939, compound

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 phenethyl-2-pyridyl-carbonate and phenethyl-2-oxopyridine 1-carboxylate (0.459 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 2M HCl solution to pH 2-3 and subsequently extracted with AcOEt (3×10 mL). The organic fraction was dried over Na2SO4, filtered and concentrated to dryness to afford the title compound (0.35 g, 89%) as transparent oil, which was used in the next step without further purification. MS (ESI) m/z: 268 [M−H]+; (ESI) m/z: 266 [M−H]−. 1H NMR (DMSO-d6): δ 1.09 (d, J=6.4 Hz, 3H), 2.89 (t, J=6.9 Hz, 2H), 3.94 (dd, J=3.4, 9.0 Hz, 1H), 4.04-4.11 (m, 1H), 4.13-4.24 (m, 2H), 6.75 (d, J=9.0 Hz, 1H), 7.20-7.33 (m, 5H) 11.95 (br s, 1H).

1. additionwas added
2. customthe crude mixture was rotary evaporated
3. customto remove the organics and
4. extractionsubsequently extracted with Et2O (3×5 mL)
5. extractionsubsequently extracted with AcOEt (3×10 mL)
6. dry with materialThe organic fraction was dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated to dryness

ORD record

ord-21e776bf882d47d28077351357c216e3

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353075B2