Tetrabutylammonium Fluoride → HCID 10295484, compound

HRID 1829806Notes

Reaction equation

HRID 1829806 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][CH2:13][CH2:14][C@@H:15]([N:26]1[CH:30]=[C:29]([C:31]([NH2:33])=[O:32])[N:28]=[CH:27]1)[C@@H:16]([O:18][Si](C(C)(C)C)(C)C)[CH3:17])[CH:6]=[CH:5]2.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][CH2:13][CH2:14][C@@H:15]([N:26]1[CH:30]=[C:29]([C:31]([NH2:33])=[O:32])[N:28]=[CH:27]1)[C@@H:16]([OH:18])[CH3:17])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 10186857HCID 10186857, compound

Product 1

HCID 10295484HCID 10295484, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice cooled solution of 1-[(2S,3R)-5-(6-bromo-2-naphthyloxy)-2-(tert-butyldimethylsilyloxy)-3-pentyl]imidazole-4-carboxamide (120 mg, 0.225 mmol) in THF (5 ml) was added dropwise 1.0 M tetra-n-butylammonium fluoride in THF (338 μl). After the addition was completed, the reaction mixture was stirred at ice-bath temperature for 2 hours. The reaction was quenched by addition of 25% aqueous AcONH4 (5 ml) and H2O (10 ml) The resulting mixture was stirred for several minutes and then extracted with ethyl acetate (30 ml). The organic layer was washed with brine, dried (sodium sulfate) and concentrated under reduced pressure. The residue was purified by silica gel (4 g) column chromatography eluting with chloroform/methanol (100:1 to 20:1) to give 1-[(2S,3R)-5-(6-bromo-2-naphthyloxy)-2-hydroxy-3-pentyl]imidazole-4-carboxamide (16) (58.6 mg, 62.2%) as a white solid.

Workup

  1. additionAfter the addition
  2. customThe reaction was quenched by addition of 25% aqueous AcONH4 (5 ml) and H2O (10 ml) The resulting mixture
  3. stirringwas stirred for several minutes
  4. extractionextracted with ethyl acetate (30 ml)
  5. washThe organic layer was washed with brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel (4 g) column chromatography
  9. washeluting with chloroform/methanol (100:1 to 20:1)

Sources & evidence

ORD record
ord-867abbd730bb4ff8983a4c6a90dc1bf8
Source dataset
uspto-grants-2006_06
Patent number
US07064144B2

Reaction notes

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