Tetrabutylammonium Fluoride Trihydrate → HCID 67520022, compound

HRID 1925525Notes

Reaction equation

HRID 1925525 reaction equation
[Si]([O:8][C@H:9]([C:34]1[CH:45]=[CH:44][C:37]2[O:38][C:39]([CH3:43])([CH3:42])[O:40][CH2:41][C:36]=2[CH:35]=1)[CH2:10][NH:11][C@H:12]([CH3:33])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]23[CH2:29][CH:24]4[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]4)[CH2:21]2)[CH2:27]3)[C:15]=1[O:30][CH2:31][CH3:32])(C(C)(C)C)(C)C.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][CH:9]([C:34]1[CH:45]=[CH:44][C:37]2[O:38][C:39]([CH3:43])([CH3:42])[O:40][CH2:41][C:36]=2[CH:35]=1)[CH2:10][NH:11][CH:12]([CH3:33])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]23[CH2:27][CH:26]4[CH2:25][CH:24]([CH2:23][CH:22]([CH2:28]4)[CH2:21]2)[CH2:29]3)[C:15]=1[O:30][CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 67520687HCID 67520687, compound

Product 1

HCID 67520022HCID 67520022, compoundYield 990%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

928 mg (1.26 mmol) of the Intermediate 83 and 794 mg (2.52 mmol) of tetrabutylammonium fluoride trihydrate in 30 ml of anhydrous THF are stirred at room temperature overnight. The solution is concentrated and the residue is partitioned in ethyl acetate/water. The organic layer is washed with water, dried and concentrated. The residue is chromatographied on silicagel using dichloromethane/methanol 90:3 as eluent to give 590 mg (990% yield) of the desired compound as a yellowish oil.

Workup

  1. concentrationThe solution is concentrated
  2. customthe residue is partitioned in ethyl acetate/water
  3. washThe organic layer is washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-47982da51ee84c89bd46aac426941666
Source dataset
uspto-grants-2012_05
Patent number
US08178679B2

Reaction notes

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