Hydrochloric Acid → (S)-3-cyclohexyl-N-[1-((R)-2,3-dihydroxy-propyl)-1H-pyrazol-3-yl]-2-(8-methoxy-3-oxo-3,9-dihydro-1H-chromeno[2,3-c]pyrrol-2-yl)-propionamide

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-3-cyclohexyl-N-[1-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrazol-3-yl]-2-(8-methoxy-3-oxo-3,9-dihydro-1H-chromeno[2,3-c]pyrrol-2-yl)-propionamide (140 mg, 0.25 mmol) in tetrahydrofuran (5 mL) was treated with 2N HCl (2.05 mL, 0.31 mmol). The mixture was stirred for 4 hours at 23° C. The reaction mixture after aqueous work-up and silica gel flash chromatography using hexane-ethyl acetate gradient elution, afforded (S)-3-cyclohexyl-N-[1-((R)-2,3-dihydroxy-propyl)-1H-pyrazol-3-yl]-2-(8-methoxy-3-oxo-3,9-dihydro-1H-chromeno[2,3-c]pyrrol-2-yl)-propionamide (68.1 mg, 52.7%), as a white solid. 1H NMR (DMSO-d6) δ: 10.80 (s, 1H), 7.52 (s, 1H), 7.22 (t, J=8.3 Hz, 1H), 6.76 (d, J=8.3 Hz, 1H), 6.68 (d, J=8.3 Hz, 1H), 6.39 (s, 1H), 4.93 (d, J=4.9 Hz, 2H), 4.70 (br. s., 1H), 4.37 (d, J=19.1 Hz, 1H), 4.09 (dd, J=13.4, 4.2 Hz, 1H), 3.99 (d, J=19.1 Hz, 2H), 3.88 (d, J=7.8 Hz, 1H), 3.83-3.86 (m, 1H), 3.76 (br. s., 2H), 3.53 (s, 3H), 1.50-1.83 (m, 7H), 0.81-1.31 (m, 6H).

Provenance & Evidence