Hydrochloric Acid → N-[(1S)-1-carboxy-2-methylpropyl]hept-6-en-1-aminium chloride

Participants

Reaction Steps

To a solution (0.4M) of methyl (2S)-2-(hept-6-en-1-ylamino)-3-methylbutanoate 67 in a 1:1 mixture of dioxane and water, LiOH (4 eq.) was added, and the reaction mixture was stirred at reflux for 24 h. The reaction mixture was then cooled and brought to pH=2 by small additions of HCl(aq) 6N. The white precipitate was filtered and washed with H2O and dried overnight. The title compound (71%) as a white precipitate was used in the next step without any further purification. 1H NMR (400 MHz, DMSO-d6, 300 K) δ 9.80 (bs, 1H), 8.95 (bs, 1H), 5.74 (ddt, J 17.0, 16.9, 6.7, 1H), 4.95 (d, J 17.0, 1H), 4.89 (d, J 10.2, 1H), 3.73-3.70 (m, 1H), 2.91-2.72 (m, 2H), 2.43-2.35 (m, 1H), 1.96 (q, J 6.7, 2H), 1.78-1.65 (m, 2H), 1.33-1.24 (m, 4H), 1.01 (d, J 7.1, 3H), 0.92 (d, J 6.8, 3H).

Provenance & Evidence