Hydrochloric Acid → HCID 86622986, compound

Participants

Reaction Steps

(1R,2R)-2-Acetyloxy-1-methylpropyl (2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoate (8) (0.4 g, 0.97 mmol) was dissolved in 8 mL of 4M HCl in 1,4-dioxane. The resulting mixture was stirred at room temperature for 60 min. After removing dioxane, acetonitrile (5 mL) was added. The title compound (5) (0.16 g, 53% yield) was crystallized and collected by filtration. 1H NMR (400 MHz, CD3OD): δ 1.19 (d, J=6.4 Hz, 3H), 1.21 (d, J=6.4 Hz, 3H), 2.04 (s, 3H), 3.02 (dd, J=12.0, 6.4 Hz, 1H), 3.07 (dd, J=12.0, 6.4 Hz, 1H), 4.21 (t, J=6.4 Hz, 1H), 4.95 (m, 1H), 5.04 (m, 1H), 6.57 (dd, J=8.0, 2.0 Hz, 1H), 6.67 (d, J=2.0 Hz, 1H), 6.74 (d, J=8.0 Hz, 1H). MS (ESI) m/z 312.2 (M+H)+ and 310.2 (M−H)−.

Provenance & Evidence