Tetrabutylammonium Fluoride → HCID 89871088, compound

HRID 516175Notes

Reaction equation

HRID 516175 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

HCID 2724141Tetrabutylammonium FluorideHCID 89871072HCID 89871072, compound

Product 1

HCID 89871088HCID 89871088, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

Workup

  1. customSilica gel was separated by filtration
  2. distillationthe solvent of the filtrate was distilled off under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bab0cd33d2494cf1895b1205d148c156
Source dataset
uspto-grants-2015_08
Patent number
US09108973B2

Reaction notes

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