Acetic Acid → HCID 86699921, compound

Temperature

0 °C

In a round bottomed flask equipped with a magnetic stirrer, (1-methylcyclohexyl)-N-aminocarbamate (0.497 g, 2.89 mmol), H2O (4 mL) and CH3COOH (0.33 mL, 5.78 mmol) were added sequentially. The mixture was cooled to 0° C. and NaNO2 (0.239 g, 3.47 mmol) dissolved in H2O (1 mL) was added dropwise. The cloudy mixture was stirred for 40 min at rt, then dioxane (10 mL) was added followed by a D-threonine salt solution [prepared from D-threonine (0.516 g, 4.33 mmol) dissolved in H2O (4 mL) and Na2CO3 (1.25 g, 11.56 mmol)]. The mixture was heated overnight at 45° C., then cooled to rt. AcOEt (50 mL) and H2O (50 mL) were added and, while maintaining a vigorous stirring, the pH was adjusted to 2 with 2M HCl solution. The two phases were separated and the aqueous phase washed again with of AcOEt (15 mL) for 10 min. The combined organic portions were dried over Na2SO4 and concentrated to give a light yellow oil (0.503 g, 67%) which was used in the next step without further purification. MS (ESI) m/z: 282.3 [M−Na]+; (ESI) m/z: 258.1 [M−H]−. 1H NMR (DMSO-d6): δ 1.09 (d, J=6.3 Hz, 3H), 1.10-1.65 (m, 8H), 1.40 (s, 3H), 2.04 (m, 2H), 3.89 (dd, J=9.3, 3.2 Hz, 1H), 4.06 (m, 1H), 6.31 (d, J=9.3, 1H), 12.08 (bs, 1H).

1. customIn a round bottomed flask equipped with a magnetic stirrer
2. additionwas added dropwise
3. temperatureThe mixture was heated overnight at 45° C.
4. temperaturecooled to rt
5. temperaturewhile maintaining a vigorous stirring
6. customThe two phases were separated
7. washthe aqueous phase washed again with of AcOEt (15 mL) for 10 min
8. dry with materialThe combined organic portions were dried over Na2SO4
9. concentrationconcentrated

ORD record

ord-df63561c4e164a25b59cfec18752b178

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353075B2