Ammonium Chloride → 3-{5-[(4R)-4-Ethyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl]-5-{[(2S)-1-methoxypropan-2-yl]oxy}phenol

HRID 1964681Notes

Reaction equation

HRID 1964681 reaction equation
[CH2:1]([C@@H:3]1[CH2:7][O:6][C:5]([C:8]2[NH:9][C:10]([C:13]3[CH:18]=[C:17]([O:19][Si](C(C)C)(C(C)C)C(C)C)[CH:16]=[C:15]([O:30][C@@H:31]([CH3:35])[CH2:32][O:33][CH3:34])[CH:14]=3)=[CH:11][CH:12]=2)=[N:4]1)[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([C@@H:3]1[CH2:7][O:6][C:5]([C:8]2[NH:9][C:10]([C:13]3[CH:18]=[C:17]([OH:19])[CH:16]=[C:15]([O:30][C@@H:31]([CH3:35])[CH2:32][O:33][CH3:34])[CH:14]=3)=[CH:11][CH:12]=2)=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 66890090(4R)-4-Ethyl-2-[5-(3-{[(2S)-1-methoxypropan-2-yl]oxy}-5-[(tripropan-2-ylsilyl)oxy]phenyl)-1H-pyrrol-2-yl]-4,5-dihydro-1,3-oxazole

Product 1

HCID 668912093-{5-[(4R)-4-Ethyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl]-5-{[(2S)-1-methoxypropan-2-yl]oxy}phenolYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4R)-4-Ethyl-2-[5-(3-{[(2S)-1-methoxypropan-2-yl]oxy}-5-[(tripropan-2-ylsilyl)oxy]phenyl)-1H-pyrrol-2-yl]-4,5-dihydro-1,3-oxazole (965 mg, 1.93 mmol) synthesized in Example (108a) was dissolved in tetrahydrofuran (10 mL), and tetrabutylammonium fluoride (1.0 mol/L tetrahydrofuran solution, 2.50 mL, 2.50 mmol) was added at room temperature, followed by stirring at room temperature for 1 hour under nitrogen atmosphere. To this reaction solution, a saturated aqueous ammonium chloride solution (30 mL) was added, and extraction was carried out with methylene chloride (40 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: methanol/methylene chloride=2%-4%) to afford the desired compound (550 mg, yield 83%) as a white solid.

Workup

  1. extractionextraction
  2. washThe organic layer was washed with saturated brine
  3. dry with materialsubsequently dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: methanol/methylene chloride=2%-4%)

Sources & evidence

ORD record
ord-5b12f794376242f3ac9754697fc0aab0
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

Loading…