N-((1S)-1-{[((1S)-3-Hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-1H-indole-2-carboxamide (43)
Following the procedure described for the preparation of N-((1S)-1-{[((1S)-3-hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide but substituting N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-1H-indole-2-carboxamide and making noncritical variations provided a crude yellow foam. This material was purified by Biotage MPLC (40 M column, 4.5–5.5% methanol/chloroform) to afford 730 mg (72%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 11.59 (s, 1H), 8.49 (d, J = 8 Hz, 1H), 8.43 (d, J = 8 Hz, 1H), 7.62 (s, 1H), 7.60 (s, 1H), 7.41 (d, J = 8 Hz, 1H), 7.23 (s, 1H), 7.17 (t, J = 8 Hz, 1H), 7.02 (t, J = 8 Hz, 1H), 5.05 (t, J = 8 Hz, 1H), 4.56 (m, 1H), 4.43 (m, 1H), 4.25 (dd, J = 8, 20 Hz, 1H), 4.13 (dd, J = 8, 20 Hz, 1H), 3.10 (m, 2H), 2.25 (m, 1H), 2.07 (m, 1H), 1.93 (m, 1H), 1.80 (m, 1H), 1.64 (m, 3H), 0.94 (s, 9H); MS (ESI+) for C24H32N4O5m/z 457.1 (M + H)+; anal. calcd for C24H32N4O5·0.2 CHCl3·0.2 ethyl acetate·0.25 H2O: C, 59.75; H, 6.88; N, 11.15. Found: C, 59.67; H, 6.72; N, 11.03; HRMS (ESI+) calcd for C24H32N4O5 457.2446, found 457.2439.