Tetrabutylammonium Fluoride → HCID 15546052, compound

HRID 2099882Notes

Reaction equation

HRID 2099882 reaction equation
C([O:5][CH2:6][C@@:7]12[CH2:34][O:33][C@@H:9]([C@:10]([SiH](C3C=CC=CC=3)C3C=CC=CC=3)([N:12]3[CH:19]=[CH:18][C:16](=[O:17])[NH:15][C:13]3=[O:14])[O:11]1)[C@@H:8]2[OH:35])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:34]1[C@@:7]2([CH2:6][OH:5])[C@@H:8]([OH:35])[C@H:9]([C@H:10]([N:12]3[CH:19]=[CH:18][C:16](=[O:17])[NH:15][C:13]3=[O:14])[O:11]2)[O:33]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride2×HCID 131727552HCID 131727552, compound

Product 1

HCID 15546052HCID 15546052, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Compound 12 (13.2 g, 26.7 mmol) was dissolved in anhydrous THF (60 mL). To this mixture was added tetrabutylammonium fluoride (TBAF, 29.4 mmol, 29.4 mL of a 1 M solution in THF). After stirring at room temperature for 2 hours, mixture was concentrated in vacuo to ˜15 mL and then eluted through a short silica gel column with 10% methanol in CH2Cl2. Eluate was concentrated to a pale solid, which was washed on a glass frit with a minimal amount of ice-cold methanol. The remaining solid was dried in vacuo to yield 5.78 g (84%) of 13 as a white solid.

Workup

  1. concentrationmixture was concentrated in vacuo to ˜15 mL
  2. washeluted through a short silica gel column with 10% methanol in CH2Cl2
  3. concentrationEluate was concentrated to a pale solid, which
  4. washwas washed on a glass frit with a minimal amount of ice-cold methanol
  5. customThe remaining solid was dried in vacuo

Sources & evidence

ORD record
ord-753cac24526e4840a4728dce1b269668
Source dataset
uspto-grants-2009_08
Patent number
US07569686B1

Reaction notes

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