Tetrabutylammonium Fluoride → HCID 89871088, compound
Reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24]([N:26]([C:68]([O:70][C:71]([CH3:74])([CH3:73])[CH3:72])=[O:69])[C:27]1[C:28]2[C:35]([I:36])=[CH:34][N:33]([C@@H:37]3[CH2:41][N:40]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C@H:39]([CH2:49][O:50][Si](C(C)(C)C)(C4C=CC=CC=4)C4C=CC=CC=4)[CH2:38]3)[C:29]=2[N:30]=[CH:31][N:32]=1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>C1COCC1>[C:19]([O:23][C:24]([N:26]([C:68]([O:70][C:71]([CH3:74])([CH3:73])[CH3:72])=[O:69])[C:27]1[C:28]2[C:35]([I:36])=[CH:34][N:33]([C@@H:37]3[CH2:41][N:40]([C:42]([O:44][C:45]([CH3:46])([CH3:47])[CH3:48])=[O:43])[C@H:39]([CH2:49][OH:50])[CH2:38]3)[C:29]=2[N:30]=[CH:31][N:32]=1)=[O:25])([CH3:20])([CH3:21])[CH3:22]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Silica gel-carrying tetrabutyl ammonium fluoride (700 mg) (up to 1.5 mmol/g) was added to a solution of (2S,4S)-tert-butyl 4-(4-(bis(tert-butoxycarbonyl)amino)-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-((tert-butyldiphenylsilyloxy)methyl)pyrrolidine-1-carboxylate (237.5 mg) obtained in Step 3 in THF (5 ml), and the resulting mixture was stirred at room temperature overnight. Silica gel was separated by filtration, and the solvent of the filtrate was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the title compound as a light-yellow, amorphous substance (185 mg). Physical properties: m/z [M+H]+ 660.2