Reaction Steps
Deprotection of 13 (250 mg, 0.69 mmol) as in Example C above and reaction of the product with EDCI.HCl (332 mg, 1.73 mmol), (E)-3-(acetylamino)cinnamic acid (148 mg, 0.72 mmol) and DMA (3 mL) at 20° C. for 3 h, followed by addition of dilute KHCO3, precipitated. This was collected, dissolved in warm EtOAc (180 mL) and filtered through a column of silica gel. Solvent concentration followed by addition of i-Pr2O precipitated the crude product which was recrystallised from EtOAc/i-Pr2O to give 14k (232 mg, 75%), mp 214-216° C. 1H NMR [(CD3)2SO] δ 10.07 (s, 1 H, NH), 9.22 (s, 1 H, H-4), 8.33 (dd, J=7.8, 1.9 Hz, 1 H, H-6), 8.19 (dd, J=7.3, 1.6 Hz, 1 H, H-9), 7.88 (s, 1 H, H-2'), 7.78-7.63 (m, 3 H, H-7,8,4'), 7.68 (d, J=15.3 Hz, 1 H, PhCH=CH), 7.55 (d, J=7.8 Hz, 1 H, H-6'), 7.39 (t, J=7.9 Hz, 1 H, H-5'), 7.14 (d, J=15.4 Hz, 1 H, PhCH=CH), 4.72-4.55 (m, 3 H, H-1,2), 4.12-4.05 (m, 2 H, CH2Cl), 2.08 (s, 3 H, CH3). Anal. Calculated for C24H20ClN3O4 : C, 64.1; H, 4.5; N, 9.2; Cl, 7.9. Found: C, 64.3; H, 4.4; N, 9.3; Cl, 7.8%.
