Tetrabutylammonium Fluoride → HCID 90412648, compound

HRID 1754600Notes

Reaction equation

HRID 1754600 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:19]([C@H:27]([CH3:73])[C@H:28]([CH2:54][N:55]1[CH:63]=[N:62][C:61]2[C:56]1=[N:57][CH:58]=[N:59][C:60]=2[NH:64][C:65](=[O:72])[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)[CH2:29][O:30][C:31]([C:46]1[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=1)([C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[Si](C(C)(C)C)(C)C>C1COCC1>[C:65]([NH:64][C:60]1[N:59]=[CH:58][N:57]=[C:56]2[C:61]=1[N:62]=[CH:63][N:55]2[CH2:54][C@@H:28]([C@H:27]([OH:19])[CH3:73])[CH2:29][O:30][C:31]([C:46]1[CH:47]=[CH:48][C:49]([O:52][CH3:53])=[CH:50][CH:51]=1)([C:38]1[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:72])[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 90411616HCID 90411616, compound

Product 1

HCID 90412648HCID 90412648, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tetrabutylammonium fluoride 1M in THF (3 ml) was added to a solution of 13 (1.1 g, 1.45 mmol) in 10 ml of THF. The reaction was kept at room temperature for 2 days until no staring material was seen by HPLC analysis. The reaction was concentrated and partitioned between water and ethyl acetate. The organic phase was washed with saturated NaCl, dried over Na2SO4 and concentrated. The resulting material was chromatographed on silica eluting with a gradient of acetone (0-40%) in ethyl acetate. Concentration of the pure product fractions afforded 0.9 g (96%) of 14 as a white amorphous solid. 1H NMR (DMSO-d6): δ 11.12 (s, 1H), 8.70 (s, 1H), 8.34 (s, 1H), 8.05 (d, J=8.7 Hz, 2H), 7.65 (m, 1H), 7.56 (t, J=7.5 Hz, 2H), 7.18 (m, 5H), 7.04 (m, 4H), 6.77 (m, 4H), 4.79 (d, J=4.8 Hz, 1H), 4.39 (m, 2H), 3.80 (m, 1H), 3.71 (s, 6H), 3.09 (m, 1H), 2.88 (m, 1H), 2.31 (m, 1H), 1.03 (d, J=6.3 Hz, 3H).

Workup

  1. concentrationThe reaction was concentrated
  2. custompartitioned between water and ethyl acetate
  3. washThe organic phase was washed with saturated NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe resulting material was chromatographed on silica eluting with a gradient of acetone (0-40%) in ethyl acetate

Sources & evidence

ORD record
ord-382fe9b8652546a8917c302a35f64fbd
Source dataset
uspto-grants-2015_10
Patent number
US09169256B2

Reaction notes

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