Hydrochloric Acid → HCID 86621599, compound

Participants

Reaction Steps

(1R)-1-Methyl-2-phenylcarbonyloxyethyl (2S)-2-[(tert-butoxy)carbonylamino]-3-[3,4-bis(2,2-dimethylpropanoyloxy)phenyl]propanoate (13) (1.03 g, 1.64 mmol) was dissolved in 20 mL of 4M HCl in dioxane. The reaction mixture was stirred at room temperature for 60 min. Dioxane was completely evaporated under reduced pressure. The resulting white solid was dissolved in water (15 mL) and washed with methyl tert-butyl ether. The aqueous phase was collected and mixed with acetonitrile (10 mL). Lyophilization gave the title compound (12) (0.851 g, 98% yield) as a white solid. 1H NMR (400 MHz, CD3OD): δ 1.30 (3H, d, J=6.4 Hz), 1.33 (9H, s), 1.34 (9H, s), 3.13 (1H, dd, J=14.4, 6.8 Hz), 3.20 (1H, dd, J=14.4, 6.4 Hz), 4.22 (1H, t, J=6.8 Hz), 4.32 (1H, dd, J=12.4, 6.4 Hz), 4.49 (1H, dd, J=12, 3.2 Hz), 5.33 (1H, m), 7.10 (1H, d, J=8 Hz), 7.11 (1H, d, J=2 Hz), 7.17 (1H, dd, J=2, 8 Hz), 7.47 (2H, t, J=7.2 Hz), 7.58 (1H, t, J=7.2 Hz), 8.02 (2H, d, J=7.6 Hz). MS (ESI) m/z 528.14 (M+H)+.

Provenance & Evidence