L-Leucine → Leucic acid, L-

Temperature

0 °C

To a stirred solution of L-Leu-OH (5.0 g, 38.2 mmol) in 1 N H2SO4 (50 mL) at 0° C. was slowly added over 11/2 h a solution of sodium nitrite (NaNO2) (7.5 g, 0.11 mmol) in water (20 mL) while maintaining the temperature at 0° C. The reaction mixture was gradually warmed to R.T., stirred for 24 h, and concentrated to give a white solid. The solid was extracted with ether (5×50 mL). The combined organic layers were dried (MgSO4), filtered and concentrated to give (2S)-2-hydroxy-4-methylpentanoic acid as an oil (4.1 g, 81.2%): 1H NMR (CDCl3, 300 MHz) δ 0.98 (d, 6H, J=12.0 Hz), 1.57-1.67 (m, 2H), 1.82-1.93 (m, 1H), 4.36 (t, 1H, J=6.0 Hz) ppm.

1. temperatureThe reaction mixture was gradually warmed to R.T.
2. concentrationconcentrated
3. customto give a white solid
4. extractionThe solid was extracted with ether (5×50 mL)
5. dry with materialThe combined organic layers were dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-0555341a620d461c9f588f474e445e7e

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06015879