Reaction Steps
Following the experimental and purification procedure of Step 2i, (1S,4R,6S,13S,17R)-7-trans-13-tert-butoxycarbonyl-amino-17-(7-methoxy-2-phenylquin-olin-4-yloxy)-2,14-dioxo-3,15-diazatricyclo-[13.3.0.04,6]octadec-7-ene-4-carboxylic acid ethyl ester (185 mg, 0.265 mmol) was reacted with 64 mg (1.6 mmol) of LiOH in 15.5 mL of 9:5:1.5 of THF/H2O/MeOH to afford (1S,4R,6S,13S,17R)-7-trans-13-tert-butoxycar-bonylamino-17-(7-methoxy-2-phenylquinolin-4-yloxy)-2,14-dioxo-3,15-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid (180 mg, 100%): 1H NMR (300 MHz, CD3OD) δ 1.14 (s, 9H), 1.20-1.51 (m, 5H), 1.53-1.58 (m, 1H), 1.70 (dd, J=9.9, 5.1 Hz, 1H), 1.86 (brs, 1H), 2.06 (brs, 1H), 2.28-2.59 (m, 3H), 2.65-2.73 (m, 1H), 3.94 (s, 3H), 4.07 (dd, J=11.3, 2.6 Hz, 1H), 4.23 (d, J=8.4 Hz, 1H), 4.64-4.70 (m, 2H), 5.54-5.68 (m, 3H), 7.10 (dd, J=9, 2 Hz, 1H), 7.26 (s, 1H), 7.39 (d, J=2.2 Hz, 1H), 8.02, 8.04 (2s, 2H), 8.12 (d, J=9.1 Hz, 1H). LC-MS (Method E-retention time: 1.57), MS m/z 685 (M++1). HRMS m/z (M+H)+ calcd for C38H45N4O8: 685.3238, found 685.3241. Step 5j: Preparation of Compound 5, Example 5 (1S,4R,6S,13S,17R)-7-trans-[4-Cyclopropanesul-fonylamino-carbonyl-17-(7-methoxy-2-phenylquinolin-4-yloxy)-2,14-dioxo-3,15-diazatricyclo[13.3.0.04,6]octa-dec-7-en-13-yl]carbamic acid tert-butyl ester
