[F:1][C:2]1[CH:3]=[C:4]([C:17]#[N:18])[CH:5]=[C:6]([B:8]2[O:12]C(C)(C)C(C)(C)[O:9]2)[CH:7]=1.I([O-])(=O)(=O)=O.[Na+].C([O-])(=O)C.[NH4+].O>CC(C)=O>[C:17]([C:4]1[CH:5]=[C:6]([B:8]([OH:12])[OH:9])[CH:7]=[C:2]([F:1])[CH:3]=1)#[N:18]
1.00 g (4.05 mmol) of the compound from Example 21A is provided in 40 ml of acetone, 2.60 g (12.1 mmol) of sodium periodate, 0.70 g (9.11 mmol) of ammonium acetate and 40 ml of water are added and the mixture is stirred at room temperature overnight. The mixture is subsequently concentrated, a 2N aqueous sodium hydroxide solution is added to the residue and the precipitate that remains is filtered off with suction. Using a concentrated aqueous hydrogen chloride solution, the solution is adjusted to pH 3 and cooled to 0° C. The precipitate formed is collected by suction filtration, washed with water and dried under high vacuum. 384 mg (58% of theory) of the title compound are obtained.
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