Hydrochloric Acid → HCID 86597964, compound

Participants

Reaction Steps

(3R,4R,5R)-3-Acetylamino-4,5-dimethyl-heptanoic acid ethyl ester (13.63 g, 56.0 mmol) was heated under reflux with 200 mL of 1M hydrochloric acid for 72 hours. The solution was cooled and extracted 2× with 50 mL aliquots of MTBE. The aqueous phase was evaporated to a semisolid. Acetonitrile (4×100 mL) was added and evaporated to give 10.75 g (89% yield) of the titled compound as a white crystalline solid: 1H NMR (CD3OD, 399.77 MHz) 0.87 (t, J=7.3 Hz, 3H), 0.94 (t, J=6.6 Hz, 6H), 1.02–1.15 (m, 1H), 1.37–1.53 (m, 2H), 1.58–1.68 (m, 1H), 2.64 (dd, J=17.5, 7.4 Hz, 1H), 2.73 (dd, J+17.5, 4.8 Hz, 1H), 3.54–3.61 (m, 1H). Low resolution mass spec: nominal m/e calc'd for C9H20ClNO2 (M+H)+: 174. Found: m/e 174.

Provenance & Evidence