Carbon Tetrachloride → 5-Methoxy-2-(5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)-1,3-oxazole

HRID 1964539Notes

Reaction equation

HRID 1964539 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([CH3:36])[O:5][C:6]1[CH:7]=[C:8]([C:23]2[NH:27][C:26]([C:28]([NH:30][CH2:31][C:32]([O:34][CH3:35])=O)=[O:29])=[CH:25][CH:24]=2)[CH:9]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.C(Cl)(Cl)(Cl)Cl>C(#N)C.O>[CH3:35][O:34][C:32]1[O:29][C:28]([C:26]2[NH:27][C:23]([C:8]3[CH:9]=[C:10]([O:12][C:13]4[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:20])=[O:21])=[CH:15][CH:14]=4)[CH:11]=[C:6]([O:5][C@@H:4]([CH3:36])[CH2:3][O:2][CH3:1])[CH:7]=3)=[CH:24][CH:25]=2)=[N:30][CH:31]=1

Participants

7

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66681479Methyl N-[(5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)carbonyl]glycinate

Product 1

HCID 580655415-Methoxy-2-(5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)-1,3-oxazoleYield 62.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Methyl N-[(5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)carbonyl]glycinate (270 mg, 0.523 mmol) synthesized in Example (24a) was dissolved in acetonitrile (10 mL), and triphenylphosphine (410 mg, 1.56 mmol), triethylamine (0.22 mL, 1.58 mmol) and carbon tetrachloride (0.33 mL, 3.42 mmol) were added, followed by stirring at room temperature for 15 hours under nitrogen atmosphere. Water (10 mL) was added, and the solution was separated with ethyl acetate (15 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%-40%) to afford the desired product (162 mg, yield 62%) as an orange solid.

Workup

  1. customthe solution was separated with ethyl acetate (15 mL)
  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: ethyl acetate/hexane=10%-40%)

Sources & evidence

ORD record
ord-aefc8784b58b4e4982a523799185b7ef
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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