Tetrahydrofuran → HCID 58542334, compound

HRID 1951895Notes

Reaction equation

HRID 1951895 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.[Si]([O:31][CH2:32][C@@H:33]1[N:40]([C:41](=[O:77])[C@@H:42]2[CH2:46][C@@H:45]([F:47])[CH2:44][N:43]2[C:48]([C:50]2[S:54][C:53]3=[N:55][C@:56]([C:67]4[CH:68]=[N:69][C:70]([Cl:73])=[CH:71][CH:72]=4)([CH3:66])[C@@H:57]([C:58]4[CH:63]=[CH:62][C:61]([Cl:64])=[C:60]([F:65])[CH:59]=4)[N:52]3[C:51]=2[CH:74]([CH3:76])[CH3:75])=[O:49])[CH2:39][C:36]2([CH2:38][CH2:37]2)[N:35](C(=O)C(F)(F)F)[CH2:34]1)(C(C)(C)C)(C)C>C(OCC)(=O)C>[Cl:64][C:61]1[CH:62]=[CH:63][C:58]([C@H:57]2[N:52]3[C:53]([S:54][C:50]([C:48]([N:43]4[CH2:44][C@H:45]([F:47])[CH2:46][C@H:42]4[C:41]([N:40]4[CH2:39][C:36]5([CH2:37][CH2:38]5)[NH:35][CH2:34][C@@H:33]4[CH2:32][OH:31])=[O:77])=[O:49])=[C:51]3[CH:74]([CH3:75])[CH3:76])=[N:55][C@:56]2([C:67]2[CH:68]=[N:69][C:70]([Cl:73])=[CH:71][CH:72]=2)[CH3:66])=[CH:59][C:60]=1[F:65]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 58542338HCID 58542338, compound

Product 1

HCID 58542334HCID 58542334, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Tetra-n-butylammonium fluoride (1 M tetrahydrofuran solution) (0.42 ml, 0.42 mmol) was added to a tetrahydrofuran (4 ml) solution of the compound (255 mg, 0.28 mmol) obtained in Step 1 above and the resulting mixture was stirred at room temperature for 3 hours. The solvent was concentrated under reduced pressure, then the residue obtained was diluted with ethyl acetate and the organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue obtained was purified by NH-silica gel column chromatography [chloroform:methanol=40:1 (v/v)] to give the title compound (102 mg, 52%) as a colorless solid.

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. customthe residue obtained
  3. washthe organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue obtained
  7. customwas purified by NH-silica gel column chromatography [chloroform:methanol=40:1 (v/v)]

Sources & evidence

ORD record
ord-41fe26c0cff4402cb01a976f9bf03235
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

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