L-Alanine → 2-Methylpropyl (2S)-2-aminopropanoate hydrochloride

Participants

Reaction Conditions

Reaction Steps

To a solution of L-alanine (11.22 mmol) in isobutanol (30 mL) at 0° C. was added SOCl2 (56.12 mmol) dropwise. The reaction mixture was stirred at 85° C. during 17 hours. The reaction was cooled down to room temperature and concentrated under reduced pressure. Co-evaporations with toluene were done and the yellow solid was washed with petroleum ether and dried under vacuum to give the expected salt in 97% yield. 1H NMR (DMSO, 400 MHz) δ (ppm) 0.89 (d, J=6.8 Hz, 6H), 1.42 (d, J=7.15 Hz, 3H), 1.91 (septuplet, J=6.71 Hz, 1H), 3.88-4 (m, 2H), 4.07 (q, J=7.16 Hz, 1H), 8.53 (brs, 3H).

Provenance & Evidence