[N+](C1C=CC(C[O:9][C:10]([C:12]2[N:13]3[CH:16]([S:17][CH:18]=2)[C:15]([CH:20](OC(=O)C)[C:21]2[CH:32]=[CH:31][C:24]4[N:25]=[C:26]5[N:30]([C:23]=4[CH:22]=2)[CH2:29][CH2:28][S:27]5)(Br)[C:14]3=[O:37])=[O:11])=CC=1)([O-])=O.[H][H]>C1COCC1.P([O-])([O-])([O-])=O>[S:27]1[C:26]2=[N:25][C:24]3[CH:31]=[CH:32][C:21](/[CH:20]=[C:15]4\[C@@H:16]5[N:13]([C:14]\4=[O:37])[C:12]([C:10]([OH:11])=[O:9])=[CH:18][S:17]5)=[CH:22][C:23]=3[N:30]2[CH2:29][CH2:28]16-[Acetoxy-(2,3-dihydro-benzo[4,5]imidazo[2,1-b]thiazol-6-yl)-methyl]-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (690 mg, 1.1 mmol) was suspended in 20 ml THF and 20 ml pH=6.5 aqueous phosphate buffer. The mixture was then subjected to 45 psi hydrogen for two hours. Then it was filtered through a pad of celite and concentrated in vacuo to remove most of the THF. The solution was then cooled to zero degree and basified to pH=8 with 1 N sodium hydroxide. Then it was purified via reverse phase HPLC using 1 liter of water followed by 5%-25% acetonitrile and water. Water was then removed through concentrate in vacuo and 32 mg of product (Yield 3%) was collected. MP: >250° C.; H-NMR (D2O): □ 7.08 (m, 6H), 7.36 (s, 1H), 4.05 (m, 2H), 3.90 (b, 1H); MS: 358.3 (M+H).
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