Water → HCID 67041082, compound

HRID 605268Notes

Reaction equation

HRID 605268 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11](F)=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=1)=[O:6].[OH-].[K+].[C:24]([NH:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=1)([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].O>CS(C)=O>[C:27]([O:26][C:24](=[O:25])[NH:31][C:32]1[CH:33]=[CH:34][C:35]([O:38][C:11]2[CH:12]=[CH:13][C:8]([NH:7][C:5](=[O:6])[C:4]3[CH:3]=[C:2]([Cl:1])[CH:20]=[C:19]([Cl:21])[CH:18]=3)=[CH:9][C:10]=2[N+:15]([O-:17])=[O:16])=[CH:36][CH:37]=1)([CH3:30])([CH3:28])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 2756771N-Boc-4-hydroxyanilineHCID 3323861HCID 3323861, compound

Product 1

HCID 67041082HCID 67041082, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of Example 254a (2.0 g, 6.1 mmol) in DMSO (50 mL) was added KOH (1.4 g, 24.3 mmol) and N-Boc-4-aminophenol (1.3 g, 6.1 mmol). The mixture was heated at 80° C. for 4 h. The reaction was cooled and poured into water. The aqueous phase was extracted with ethyl acetate (2×). The combined organic phases were washed with water, brine, and dried over sodium sulfate, filtered and concentrated under vacuum giving the title compound. The residue was purified by silica gel chromatography eluting with hexanes/ethyl acetate/methanol (80:10:10) to give the desired product (1.6 g, 51%).

Workup

  1. temperatureThe reaction was cooled
  2. extractionThe aqueous phase was extracted with ethyl acetate (2×)
  3. washThe combined organic phases were washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e63926db10e4469a975be0079803f0a9
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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