Hydrochloric Acid → HCID 51348956, compound

Participants

Reaction Steps

A solution of ((1S,2S)-1-{[(4′-methoxymethyl-biphenyl-4-yl)-(2-pyridin-2-yl-cyclopropanecarbonyl)-amino]-methyl}-2-methyl-butyl)-carbamic acid tert-butyl ester (25 mg, 0.045 mmol) and dichloromethane (4 mL) was treated with a solution of HCl in dioxane (4 N, 0.5 mL) and the resulting reaction mixture was maintained at room temperature for 12 h. The reaction was then concentrated to dryness to afford (1R,2R)-2-pyridin-2-yl-cyclopropanecarboxylic acid ((2S,3S)-2-amino-3-methyl-pentyl)-(4′-methoxymethyl-biphenyl-4-yl)-amide (18 mg, 95% yield) as a white solid: 1H NMR (400 MHz, MeOD) δ 8.49 (d, J=5.8 Hz, 1H), 8.23 (t, J=7.8 Hz, 1H), 7.61-7.71 (m, 3H), 7.44-7.54 (m, 5H), 7.34 (d, J=8.1 Hz, 2H), 4.40 (s, 2H), 4.22 (dd, J=14.9, 9.1 Hz, 1H), 3.70 (dd, J=14.9, 2.5 Hz, 1H), 3.62-3.66 (m, 1H), 3.54-3.59 (m, 1H), 3.46-3.50 (m, 1H), 3.31 (s, 3H), 2.83-2.90 (m, 1H), 2.07-2.13 (m, 1H), 1.84-1.92 (m, 1H), 1.64-1.74 (m, 1H), 1.60 (dt, J=8.7, 5.5 Hz, 1H), 1.24-1.36 (m, 1H), 1.06-1.22 (m, 1H), 0.88 (d, J=6.8 Hz, 3H), 0.76 (t, J=7.3 Hz, 3H); LRMS (ESI) m/e 458.1 [(M+H)+, calcd for C29H36N3O2 458.3].

Provenance & Evidence