Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 4-chlorosalicylic acid and making noncritical variations provided a crude brown syrup. This material was purified by Biotage MPLC (25 M, 2–3% methanol/dichloromethane) to afford 64 mg (25%) of the title compound as a tan solid. 1H NMR (DMSO-d6) δ 11.58 (s, 1H), 10.50 (bs, 1H), 8.65 (d, J = 8 Hz, 1H), 8.46 (d, J = 8 Hz, 1H), 7.81 (d, J = 8 Hz, 1H), 7.63 (m, 1H), 7.37 (s, 1H), 7.08 (m, 2H), 7.00 (m, 2H), 6.50 (d, J = 8 Hz, 1H), 5.16 (d, J = 16 Hz, 2H), 5.11 (d, J = 16 Hz, 2H), 4.49 (m, 2H), 3.87 (s, 3H), 3.13 (m, 2H), 2.32 (m, 1H), 2.11–1.98 (m, 2H), 1.76–1.55 (m, 5H), 0.94 (d, J = 6 Hz, 3H), 0.89 (d, J = 6 Hz, 3H); MS (ESI-) for C31H35ClN4O8m/z 625.1 (M – H)−; anal. calcd for C31H35ClN4O8·0.1 H2O·0.14 CHCl3: C, 57.93; H, 5.52; N, 8.68. Found: C, 58.04; H, 5.78; N, 8.74; HRMS (ESI+) calcd for C31H35ClN4O8+H1 627.2216, found 627.2219.