Hydrochloric Acid → HCID 66951003, compound

Participants

Reaction Steps

(1R)-2-Acetyloxy-1-methylethyl (2S)-3-[3,4-bis(ethoxycarbonyloxy)phenyl]-2-[(tert-butoxy)carbonylamino]propanoate (20) (11.5 g, 21.2 mmol) was dissolved in 60 mL of 4M HCl in dioxane. The resulting mixture was stirred at room temperature for 60 min. Solvent removal under reduced pressure gave 10.1 g (100% yield) of the title compound (14) as a colorless oil. 1H NMR (400 MHz, CD3OD): δ 1.21 (d, J=6.4 Hz, 3H), 1.35 (t, J=7.2 Hz, 3H), 1.36 (t, J=7.2 Hz, 3H), 2.04 (s, 3H), 3.26 (d, J=7.2 Hz, 2H), 4.05 (dd, J=8.8, 6.4 Hz, 1H), 4.23 (dd, J=12.4, 3.2 Hz, 1H), 4.28 (q, J=6.8 Hz, 2H), 4.30 (q, J=6.8 Hz, 2H), 4.37 (t, J=7.2 Hz, 1H), 5.19 (m, 1H), 7.27 (dd, J=8.0, 2.0 Hz, 1H), 7.30 (d, J=2.0 Hz, 1H), 7.32 (d, J=8.0 Hz, 1H). MS (ESI) m/z 442.1 (M+H)+.

Provenance & Evidence