Reaction Steps
A suspension of the product of Example 51 (316 mg, 0.519 mmol) and 81 mg of 10% Pd/C in EtOAc (65 mL) was shaken under 50 psi of H2 on a Parr Hydrogenator for 3 h. The suspension was then filtered through Celite and the filtrate concentrated in vacuo to give 325 mg of the product as a clear oil. This residue was purified by preparative HPLC (Zorbax-RX-C8 column; 45% MeCN/55% 0.1% TFA H2O; 4.2 mL/min) and the free base subsequently converted to the HCl salt to furnish the product as a colorless foam: mp 110°-130° C. (sintered); 1H NMR (CDCl3) δ10.62 (br s, 1H). 8.53 (br s, 1H), 7.34 (d, 1H, J=7.6 Hz), 7.12 (m, 3H), 7.00 (t, 1H, J=7.6 Hz), 6.86 (d, 1H, J=7.5 Hz), 6.68 (m, 4H), 4.90 (s, 1H), 3.82 (t, 2H, J=6.5 Hz), 3.54 (s, 6H), 3.45 (m, 2H), 3.20 (m, 2H), 2.75 (m, 4H), 2.62 (m, 3H), 2.25 (s, 6H), 1.92 (m, 4H), 1.72 (h, 2H, J=6.8 Hz), and 0.95 (t, 3H, J=7.3 Hz); 13C NMR (CDCl3) δ168.4, 159.4, 157.1, 148.8, 145.5, 144.4, 139.6, 129.8, 128.5, 122.0, 118.7, 118.1, 117.2, 113.6, 112.5, 102.9, 69.5, 55.2, 53.3, 51.0, 40.2, 39.1, 36.7, 30.2, 25.1, 22.6, 19.2, and 10.5. Anal. Calcd for C35H46N4O6.HCl.0.45H2O: C, 63.37; H, 7.28; N, 8.45. Found: C, 63.37; H, 7.40; N, 8.28.
