Water → HCID 66681701, compound

HRID 1964523Notes

Reaction equation

HRID 1964523 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([CH3:35])[O:5][C:6]1[CH:7]=[C:8]([C:23]2[N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:25]=[CH:26][CH:27]=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.[Br:36]N1C(=O)CCC1=O.O>O1CCCC1>[Br:36][C:25]1[N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:23]([C:8]2[CH:9]=[C:10]([O:12][C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[CH:11]=[C:6]([O:5][C@@H:4]([CH3:35])[CH2:3][O:2][CH3:1])[CH:7]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 66683402HCID 66683402, compound

Product 1

HCID 66681701HCID 66681701, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

t-Butyl 2-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-1-carboxylate (2.70 g, 5.38 mmol) synthesized in Example (13b) was dissolved in tetrahydrofuran (50 mL), and cooled to 0° C. After addition of N-bromosuccinimide (960 mg, 5.38 mmol) with stirring under nitrogen atmosphere, stirring was carried out at room temperature for 4 hours. Water (50 mL) was added, and extraction was carried out with ethyl acetate (50 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=20%-40%) to afford the desired compound (2.93 g, yield 94%) as a brown oil.

Workup

  1. stirringstirring
  2. extractionextraction
  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=20%-40%)

Sources & evidence

ORD record
ord-f17e806f9a4d477db87372bb2ae134e6
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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