D-Threonine → HCID 86699952, compound

To a stirred mixture of D-threonine (0.15 g, 1.25 mmol) and NaHCO3 (0.158 g, 1.89 mmol) in H2O (3.5 mL), the crude mixture containing heptyl-2-pyridyl-carbonate and heptyl-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 (0.3 g, 91%) as transparent oil, which was used in the next step without further purification. 1H NMR (DMSO-d6) δ 0.86 (t, J=6.8 Hz, 3H), 1.08 (d, J=6.4 Hz, 3H), 1.18-1.36 (m, 8H), 1.46-1.61 (m, 2H), 3.87-4.01 (m, 3H), 4.01-4.14 (m, 1H), 6.67 (d, J=9.0 Hz, 1H) 12.20 (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 EtOAc (3×10 mL)
6. dry with materialThe organic fraction was dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated to dryness

ORD record

ord-29619ace117d4865a544b117800ba52d

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353075B2