O=C1[CH:8]2[CH:3]1[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7]2.C[OH:17].[Cl-].[NH4+].[N-:20]=[N+:21]=[N-:22].[Na+]>O>[N:20]([CH:3]1[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][CH:8]1[OH:17])=[N+:21]=[N-:22]To the solution of tert-butyl 7-oxo-3-azabicyclo[4.1.0]heptane-3-carboxylate (180.6 g, 0.60 mol) obtained in Step 2 in a mixed solvent of 700 ml of methanol and 100 ml of water, were added ammonium chloride (NH4Cl; 64.0 g, 1.2 mol) and sodium azide (NaN3; 98.0 g, 1.5 mol). The reaction mixture was refluxed for 8 hours and evaporated under reduced pressure to remove methanol. The resulting residue was extracted with ethyl acetate and then dried on magnesium sulfate. The resulting residue was purified with column chromatography to give the titled compound (62.0 g).
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