[F-].[K+].[Br:3][C:4]1[N:9]=[C:8]([C:10]2([CH3:25])[CH2:12][N@@:11]2[S:13]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[C:7]([F:26])=[C:6]([Si](CC)(CC)CC)[CH:5]=1.CC(O)=O.C([O-])(O)=O.[Na+]>C1COCC1.CC(OC)(C)C.CN(C=O)C>[Br:3][C:4]1[N:9]=[C:8]([C:10]2([CH3:25])[CH2:12][N@@:11]2[S:13]([C:16]2[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=2)(=[O:14])=[O:15])[C:7]([F:26])=[CH:6][CH:5]=1
Potassium fluoride (1.1 g, 18.85 mmol) was added to a solution of 6-bromo-3-fluoro-2-[(S)-2-methyl-1-(4-nitro-benzenesulfonyl)-aziridin-2-yl]-4-triethylsilanyl-pyridine (5 g, 9.43 mmol) and AcOH (1.13 g, 9.43 mmol) in 25 ml THF. DMF (35 ml) was added and the suspension was stirred for 1 h at rt. The reaction mixture was poured onto a mixture of sat. aq. NaHCO3 and TBME. The layers were separated and washed with brine and TBME. The combined organic layers were dried over MgSO4.H2O, filtered and evaporated to give a yellow oil which was crystallized from TBME/hexane to yield 3.45 g of the title compound as white crystals.
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