S(Cl)(Cl)=O.Cl.[CH3:6][O:7][C:8](=[O:15])[CH2:9][CH2:10][C@H:11]([NH2:14])[CH2:12][F:13].C(Cl)(Cl)Cl.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CO.C(N(CC)CC)C>[C:20]([NH:14][C@H:11]([CH2:12][F:13])[CH2:10][CH2:9][C:8]([O:7][CH3:6])=[O:15])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=11.0 ml of thionyl chloride was added drop-by-drop to a stirred mixture of 650 mg of 4 in 2.5 ml of methanol at room temperature. The resulting mixture was stirred at room temperature for 10 minutes, at reflux for two hours, cooled and stripped of solvent. The residue was mixed with 25 ml of chloroform and the mixture was stirred while 0.47 ml of benzoyl chloride was added drop-by-drop, then 1.2 ml of triethylamine was added, drop-by-drop. The mixture was stirred at room temperature for 16 hours, and the solvent was evaporated. The residue was mixed with 25 ml of water and the mixture was extracted with chloroform. The extract was washed successively with 1N hydrochloric acid, water, 1M sodium bicarbonate solution, and water. It then was dried (MgSO4), the solvent was evaporated, and the residue was recrystallized from methylene chloride/hexane to give 24, as fine white needles, m.p.: 99.5°-100.5° C.
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