[O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][NH2:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](Cl)(=[O:20])[CH2:18][CH3:19]>C(Cl)Cl.N1C=CC=CC=1.C(OCC)(=O)C>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][NH:16][C:17](=[O:20])[CH2:18][CH3:19])=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1To the solution of crude amine resulting from Example 67E in methylene chloride (20 mL) and pyridine (5 mL) was added propionyl chloride (3.0 mL, 34 mmol). After 6 hours, the reaction was diluted with ethyl acetate (80 mL), washed with water (20 mL), 10% aqueous hydrochloric acid (20 mL), water (20 mL), saturated copper sulfate (20 mL) and brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography eluting with 50% ethyl acetate in hexane to give the desired product (1.23 g, 27% for the last 4 steps). 1H NMR (300 MHz, CDCl3) δ 7.36-6.95 (m, 9 H), 5.46 (bs, 1 H), 3.51 (q, 2 H), 2.80 (t, 2 H), 2.19 (q, 2 H), 1.15 (t, 3 H).
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