Reaction Steps
A solution of (E)-(2R,5S,11S,14S,17R,18R)-11-(3-hydroxy-benzyl)-14-isopropyl-18-methoxy-2,17-dimethyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1(27),21,23,25-tetraene-4,10,13,16-tetraone (12 mg, 0.0185 mmol) in ethyl acetate (2 mL) containing 10% palladium on carbon (10 mg) was hydrogenated at room temperature and pressure for 1 hour. The reaction mixture was filtered through filter aid and the filter pad was washed with ethyl acetate. The filtrate was evaporated and the residue was purified by silica gel chromatography using iso-hexanes/ethyl acetate 4:6 to afford the title compound (5.6 mg, 47%) as a white solid. 1H NMR (300 MHz, CD3CN) δ0.95 (d, J=6.7 Hz, 6H), 1.28 (d, J=7.4 Hz, 3H), 1.54 (d, J=6.7 Hz, 3H), 1.30-2.30 (m, 13H), 2.55-2.60 (m, 1H), 2.75-2.91 (m, 3H), 3.26-3.32 (m, 1H), 3.44 (s, 3H), 3.50-3.57 (m, 1H), 4.00 (d, J=11.4 Hz, 1H), 4.17-4.30 (m, 2H), 5.48-5.56 (m, 1H), 5.77 (q, J=6.5 Hz, 1H), 6.66 (dd, J=8.0, 1.6 Hz, 1H), 6.88 (d, J=7.6 Hz, 1H), 7.02-7.15 (m, 7H), 7.22 (d, J=7.6 Hz, 1H), 7.95-8.05 (br s, 1H). LCMS (m/z) 651 [M+H], Tr=5.20 min.
