CC([NH:5][S:6]([C:9]1[C:14]([S:15]([CH2:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=1)(=[O:8])=[O:7])(C)C.ClC1C=CC=C(C(OO)=[O:28])C=1.O>C(Cl)Cl.FC(F)(F)C(O)=O>[CH2:17]([S:15]([C:14]1[C:9]([S:6]([NH2:5])(=[O:7])=[O:8])=[N:10][CH:11]=[CH:12][CH:13]=1)(=[O:16])=[O:28])[CH2:18][CH3:19]To a stirred solution of 8.8 g (0.029 mol) of the product from Example 3 in 400 mls methylene chloride cooled to -5°, under nitrogen, was added 6.6 g (0.038 mol) of 3-chloroperbenzoic acid and stirred at room temperature for 20 hours. The reaction mixture was poured into water and extracted with methylene chloride. The organic layers were combined and washed with saturated sodium bisulfite and brine, dried over magnesium sulfate, and evaporated to a solid mixture which was washed with hexanes to afford a white solid. The solid was dissolved and stirred in 150 mls trifluoroacetic acid for 72 hours. The solution was evaporated and triturated with ether to afford 5.3 g (46%) white solid: m.p. 153°-157°; NMR (CDCl3, 200 MHz) 1.06 (3H, t, J=7 Hz), 1.8 (2H, m), 3.7 (2H, m) 5.8 (NH2), 7.8 (1H, m), 8.6 (1H, m), 8.95 (1H, m); IR (nujol) 3390, 3180, 1360, 1310, 1175, 1150 cm-1.
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