Water → HCID 86650596, compound

Reaction equation

[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([C:15]2[N:16]=[C:17]([CH2:20][N:21]3[CH:25]=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:23]=[N:22]3)[S:18][CH:19]=2)[CH:6]=[C:7]([C:9]#[C:10][Si](C)(C)C)[CH:8]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[C:9]([C:7]1[CH:6]=[C:5]([C:15]2[N:16]=[C:17]([CH2:20][N:21]3[CH:25]=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:23]=[N:22]3)[S:18][CH:19]=2)[CH:4]=[C:3]([C:2]([F:31])([F:32])[F:1])[CH:8]=1)#[CH:10]

Participants

Procedure

Under a nitrogen atmosphere at 0° C., to a solution (20 mL) of the compound (2.1 g, 4.4 mmol) obtained in Example 98a in tetrahydrofuran was added tetrabutylammonium fluoride (1M tetrahydrofuran solution, 6.5 mL, 6.5 mmol), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=70/30) to give the title compound (940 mg, 53%) as orange crystals.