Tetrabutylammonium Fluoride → 3-[(1S)-2-Methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenol

HRID 1964702Notes

Reaction equation

HRID 1964702 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([CH3:34])[O:5][C:6]1[CH:7]=[C:8]([C:23]2[NH:27][C:26]([C:28]3[O:29][C@@H:30]([CH3:33])[CH2:31][N:32]=3)=[CH:25][CH:24]=2)[CH:9]=[C:10]([O:12][Si](C(C)C)(C(C)C)C(C)C)[CH:11]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][CH2:3][C@H:4]([CH3:34])[O:5][C:6]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]([C:23]2[NH:27][C:26]([C:28]3[O:29][C@@H:30]([CH3:33])[CH2:31][N:32]=3)=[CH:25][CH:24]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66682674(5S)-2-(5-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[(triisopropylsilyl)oxy]phenyl}-1H-pyrrol-2-yl)-5-methyl-4,5-dihydro-1,3-oxazole

Product 1

HCID 666811783-[(1S)-2-Methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenolYield 83.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(5S)-2-(5-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[(triisopropylsilyl)oxy]phenyl}-1H-pyrrol-2-yl)-5-methyl-4,5-dihydro-1,3-oxazole (29.5 g, 60.7 mmol) synthesized in Example (116c) was dissolved in tetrahydrofuran (400 mL), and tetrabutylammonium fluoride (1.0 mol/L tetrahydrofuran solution, 66 mL, 66 mmol) was added, followed by stirring for 1 hour under nitrogen atmosphere. The solvent was distilled off under reduced pressure, water (400 mL) was added to the residue, and extraction was carried out twice with ethyl acetate (400 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-50%) to afford the desired compound (16.7 g, yield 83%) as a white solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, water (400 mL)
  2. additionwas added to the residue, and extraction
  3. washThe organic layer was washed with saturated brine
  4. dry with materialsubsequently dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified
  7. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-50%)

Sources & evidence

ORD record
ord-3467c382aa074995b347e9ade2128127
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

Loading…