Ammonium Chloride → {(5R)-2-[5-(3-[(1S)-2-Methoxy-1-methylethoxy]-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}phenyl)-1H-pyrrol-2-yl]-4,5-dihydro-1,3-oxazol-5-yl}methanol

HRID 1964629Notes

Reaction equation

HRID 1964629 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]([O:6][C:7]1[CH:8]=[C:9]([CH:21]=[C:22]([C:24]2[NH:25][C:26]([C:29]3[O:30][C@@H:31]([CH2:34][O:35][Si](C(C)C)(C(C)C)C(C)C)[CH2:32][N:33]=3)=[CH:27][CH:28]=2)[CH:23]=1)[O:10][C:11]1[CH:12]=[CH:13][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[N:15][CH:16]=1)[CH3:5].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][CH2:3][C@H:4]([CH3:5])[O:6][C:7]1[CH:23]=[C:22]([C:24]2[NH:25][C:26]([C:29]3[O:30][C@@H:31]([CH2:34][OH:35])[CH2:32][N:33]=3)=[CH:27][CH:28]=2)[CH:21]=[C:9]([O:10][C:11]2[CH:16]=[N:15][C:14]([S:17]([CH3:20])(=[O:18])=[O:19])=[CH:13][CH:12]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 666810925-(3-{[(2S)-1-Methoxypropan-2-yl]oxy}-5-{5-[(5R)-5-{[(tripropan-2-ylsilyl)oxy]methyl}-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenoxy)-2-(methylsulfonyl)pyridine

Product 1

HCID 58065486{(5R)-2-[5-(3-[(1S)-2-Methoxy-1-methylethoxy]-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}phenyl)-1H-pyrrol-2-yl]-4,5-dihydro-1,3-oxazol-5-yl}methanolYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(3-{[(2S)-1-Methoxypropan-2-yl]oxy}-5-{5-[(5R)-5-{[(tripropan-2-ylsilyl)oxy]methyl}-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenoxy)-2-(methylsulfonyl)pyridine (1.18 g, 1.79 mmol) synthesized in Example (82a) was dissolved in tetrahydrofuran (10 mL), and tetrabutylammonium fluoride (1.0 mol/L tetrahydrofuran solution, 2.00 mL, 2.00 mmol) was added at room temperature, followed by stirring at room temperature for 30 minutes under nitrogen atmosphere. To this reaction solution, a saturated aqueous ammonium chloride solution (20 mL) was added, and extraction was carried out with methylene chloride (20 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%-3%) to afford the desired compound (680 mg, yield 76%) 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%-3%)

Sources & evidence

ORD record
ord-2448ab5eb3b3488da3d8efaf26a7d07f
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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