Tetrabutylammonium Fluoride → HCID 86728590, compound

HRID 1410304Notes

Reaction equation

HRID 1410304 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[C@@H:22]1[O:27][C@H:26]([CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[C@@H:25]([O:53][CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[C@H:24]([O:61][CH2:62][C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[C@H:23]1[O:69][CH2:70][C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1)[CH:2]=[CH2:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH3:21])=[CH:17][CH:18]=2)=[CH:7][C:6]=1[C@@H:22]1[O:27][C@H:26]([CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35])[C@@H:25]([O:53][CH2:54][C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[C@H:24]([O:61][CH2:62][C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[C@H:23]1[O:69][CH2:70][C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86728589HCID 86728589, compound

Product 1

HCID 86728590HCID 86728590, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-(((2R,3R,4R,5S,6S)-6-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-3,4,5-tris(benzyloxy)tetrahydro-2H-pyran-2-yl)methoxy)pentyloxy)(tert-butyl)diphenylsilane (28, 664 mg, 0.626 mmol) from Step 1 in tetrahydrofuran (8 mL) was added tetrabutylammonium fluoride (1.0 M in tetrahydrofuran, 1.9 mL, 1.88 mmol) and the reaction mixture was stirred at ambient temperature for 2 h. After removal of organic volatiles under reduced pressure, the residue was partitioned between ethyl acetate and saturated ammonium chloride solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude residue was purified on Biotage® purification apparatus (silica gel, 10 to 60% tetrahydrofuran in hexanes) to yield the title compound (29, 479 mg, 0.583 mmol, 93%) as colorless oil.

Workup

  1. customAfter removal of organic volatiles under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and saturated ammonium chloride solution
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified on Biotage® purification apparatus (silica gel, 10 to 60% tetrahydrofuran in hexanes)

Sources & evidence

ORD record
ord-d4cdedf99cb54e1382ccea521878106d
Source dataset
uspto-grants-2014_12
Patent number
US08921412B2

Reaction notes

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