[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7](=[O:31])[C@H:8]1[CH2:12][C@@H:11](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:10][N:9]1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].O>CN(C)C=O>[CH3:5][O:6][C:7](=[O:31])[C@H:8]1[CH2:12][C@H:11]([N:1]=[N+:2]=[N-:3])[CH2:10][N:9]1[C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25]Sodium azide (515 mg) was added to a stirred solution of N-tert-butoxycarbonyl-cis-4-(p-toluenesulfonyloxy)-D-proline methyl ester (B, 1.65 g) in N,N-dimethylformamide (10 mL)-water (2 mL). After stirring at 80-90° C. for 1 hr, the solvents were removed in vacuo. The residue was diluted with ethyl acetate and washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo to give the title compound (1.04 g) as a colorless oil.
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