Tetrabutylammonium Fluoride → HCID 86586949, compound

HRID 1167275Notes

Reaction equation

HRID 1167275 reaction equation
[CH2:1]([C@H:8]([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])[C@@H:9]([OH:37])[CH:10]([NH:25][S:26]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)(=[O:28])=[O:27])[CH2:11][C:12]([CH3:24])([CH3:23])[CH2:13][CH2:14][O:15][Si](C(C)(C)C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([C@H:8]([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])[C@@H:9]([OH:37])[CH:10]([NH:25][S:26]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)(=[O:28])=[O:27])[CH2:11][C:12]([CH3:24])([CH3:23])[CH2:13][CH2:14][OH:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131724065HCID 131724065, compound

Product 1

HCID 86586949HCID 86586949, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the product of Step 3 (3.47 g, 5.2 mmol) in tetrahydrofuran (25 mL) was added tetrabutylammonium fluoride (6.2 mL, 1M in tetrahydrofuran) over 15 minutes. After stirring at ambient temperature for 2 hours, the reaction was concentrated in vacuo and partitioned in ether/water (1:1; 200 mL). The layers were separated and the aqueous phase was extracted with ether (50 mL). The combined organic layers were washed with water (100 mL), dried (magnesium sulfate), concentrated in vacuo and purified by silica gel chromatography (4% methanol in chloroform) to afford the title compound (2.78 g, 97%) as a white foam.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. custompartitioned in ether/water (1:1; 200 mL)
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with ether (50 mL)
  5. washThe combined organic layers were washed with water (100 mL)
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated in vacuo
  8. custompurified by silica gel chromatography (4% methanol in chloroform)

Sources & evidence

ORD record
ord-a6d3eb2a47164ce9983984ea07302045
Source dataset
uspto-grants-2003_09
Patent number
US06617350B2

Reaction notes

Loading…