Reaction Steps
Step 29i) Following an analogous experimental and purification procedure to Step 1i, (1S,4R,6S,14S,18R)-7-cis-18-[2-(2-Acetylaminothiazol-4-yl)-7-methoxy-quinolin-4-yloxy]-14-tert-butoxycarbonylamino-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic ethyl ester (180 mg, 0.228 mmol) in 14 mL of THF and 3.5 mL of MeOH was reacted with 92 mg (2.3 mmol) of LiOH in 7 mL of H2O to afford (1S,4R,6S,14S,18R)-7-cis-18-[2-(2-Acetylaminothiazol-4-yl)-7-methoxyquinolin-4-yloxy]-14-tert-butoxycar-bonylamino-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]-nonadec-7-ene-4-carboxylic acid (150 mg, 86%): 1H NMR (500 MHz, CD3OD, some minor broadening due to rotomers) δ 11.29 (s, 9H), 1.41 (m, 7H), 1.62 (m, 2H), 1.84 (m, 1H), 1.96 (m, 1H), 2.18 (m, 1H), 2.24 (s, 3H), 2.50 (m, 1H), 2.62 (m, 1H), 2.68 (m, 1H), 3.96 (s, 3H), 4.11 (s, 1H), 4.29 (s, 1H), 4.65 (s, 2H), 5.51 (s, 3H), 7.05 (s, 1H), 7.37 (s, 1H) 7.55 (s, 1H), 7.95 (s, 1H), 8.12 (s, 1H): LC-MS m/e 763 (retention time: 3.09, method D, except gradient time increased from 2 to 4 min). Step 29j: Preparation of Compound 28, Example 29, (1S,4R,6S,14S,18R)-7-cis-{18-[2-(2-Acetylaminothiazol-4-yl)-7-methoxyquinolin-4-yloxy]-4-cyclopropanesulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo-[14.3.0.04,6]nonadec-7-en-14-yl}carbamic acid tert-butyl ester
