Tetrabutylammonium Fluoride → HCID 44200307, compound

HRID 1254638Notes

Reaction equation

HRID 1254638 reaction equation
[Si]([O:8][C@@H:9]([CH3:41])[C@@H:10]([NH:30][C:31]1[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[C:33]([Cl:39])[C:32]=1[CH3:40])[C:11]1[O:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][Si](C(C)(C)C)(C)C)[CH:17]=2)=[N:14][N:15]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOC(C)=O>[Cl:39][C:33]1[C:32]([CH3:40])=[C:31]([NH:30][C@@H:10]([C:11]2[O:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=3)=[N:14][N:15]=2)[C@@H:9]([OH:8])[CH3:41])[CH:38]=[CH:37][C:34]=1[C:35]#[N:36]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67005760HCID 67005760, compound2×

Product 1

HCID 44200307HCID 44200307, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a 25 mL round bottom flask equipped with a magnetic stirrer and a septum was added 4-((1R,2S)-2-(tert-butyldimethylsilyloxy)-1-(5-(3-(tert-butyldimethyl-silyloxy)phenyl)-1,3,4-oxadiazol-2-yl)propylamino)-2-chloro-3-methylbenzonitrile (intermediate 7c) (62 mg, 0.1 mmol), which was then dissolved in anhydrous THF (3 mL) under an atmosphere of nitrogen. To this was added the tetrabutylammonium fluoride as a 1M solution in THF (0.4 mL, 0.4 mmol) producing an instant color change to yellow. This was allowed to stir at room temperature for a period of 4 h. The solvent was then removed under reduced pressure to yield a black residue. This residue was taken up in EtOAc (20 mL) and washed with water (2×10 mL), brine (1×10 mL) and dried over Na2SO4. The solution was then filtered and concentrated under reduced pressure using rotary evaporation to reveal a yellow solid. This was purified via silica gel chromatography eluted with 70% EtOAc/hexanes to provide the title compound as a white solid (31 mg, 81%). 1H NMR (500 MHz, acetone-d6, δ in ppm) 8.88 (br s, 1H), 7.48 (m, 3H), 7.38 (m, 1H), 7.06 (m, 1H), 6.86 (d, J=8.8 Hz, 1H), 5.68 (d, J=8.5 Hz, 1H), 5.10 (dd, J=3.6, 8.5 Hz, 1H), 4.83 (br s, 1H), 4.62 (m, 1H), 2.40 (s, 3H), 1.41 (d, J=6.3 Hz, 3H).

Workup

  1. customTo a 25 mL round bottom flask equipped with a magnetic stirrer
  2. customproducing an instant color change to yellow
  3. customThe solvent was then removed under reduced pressure
  4. customto yield a black residue
  5. washwashed with water (2×10 mL), brine (1×10 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationThe solution was then filtered
  8. concentrationconcentrated under reduced pressure
  9. customevaporation
  10. customThis was purified via silica gel chromatography
  11. washeluted with 70% EtOAc/hexanes

Sources & evidence

ORD record
ord-2ba01c64f44e4fb591c4b98ca55d77d9
Source dataset
uspto-grants-2013_06
Patent number
US08455525B2

Reaction notes

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