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

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).

1. additionwas added
2. temperatureat reflux for 24 h
3. temperatureThe reaction mixture was then cooled
4. filtrationThe white precipitate was filtered
5. washwashed with H2O
6. customdried overnight
7. customThe title compound (71%) as a white precipitate was used in the next step without any further purification

ORD record

ord-7a120a7ffa734d689f4c36e07de7576f

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08314062B2