Tetrabutylammonium Fluoride → HCID 178483324, compound

HRID 976340Notes

Reaction equation

HRID 976340 reaction equation
[F:1][C:2]([F:48])([F:47])[C:3]1[CH:4]=[C:5]([C@H:13]([O:23][C@H:24]2[O:29][CH2:28][CH2:27][N:26]([CH2:30][C:31]3[N:32]=[N:33][NH:34][C:35]=3[CH2:36][N:37]([CH3:39])[CH3:38])[C@H:25]2[C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=2)[CH2:14][O:15][Si](C(C)(C)C)(C)C)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:48][C:2]([F:1])([F:47])[C:3]1[CH:4]=[C:5]([C@H:13]([O:23][C@H:24]2[O:29][CH2:28][CH2:27][N:26]([CH2:30][C:31]3[N:32]=[N:33][NH:34][C:35]=3[CH2:36][N:37]([CH3:39])[CH3:38])[C@H:25]2[C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=2)[CH2:14][OH:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178483325HCID 178483325, compound

Product 1

HCID 178483324HCID 178483324, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The product of Step C, above, (0.2 g) was stirred in anhydrous tetrahydrofuran (2 ml) with tetrabutylammonium fluoride (1.0M) in tetrahydrofuran (0.42 ml) for 30 minutes. The mixture was partitioned between ammonium chloride solution and ethylacetate, and the organic layer washed (H2O, brine), dried (MgSO4) and evaporated in vacuo. Purification by gravity silica column eluting with 4-10% MeOH/0.1% NH4OH/dichloromethane afforded the title compound. 1H NMR (250 MHz, CDCl3) δ 2.26 (6H, s), 2.51 (1H, m), 3.09 (2H, m), 3.35 (2H, m), 3.51-3.63 (4H, m), 3.78 (2H, d, J=13.8 Hz), 4.30-4.36 (2H, m), 4.88 (1H, m), 7.01-7.10 (4H, m), 7.50 (2H, vbr s), 7.59 (1H, br s).

Workup

  1. customThe mixture was partitioned between ammonium chloride solution and ethylacetate
  2. washthe organic layer washed (H2O, brine)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customPurification by gravity silica column
  6. washeluting with 4-10% MeOH/0.1% NH4OH/dichloromethane

Sources & evidence

ORD record
ord-148dadcb494a4f07b06b96d153601c34
Source dataset
uspto-grants-1997_03
Patent number
US05612337

Reaction notes

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