Dichloromethane → HCID 57972109, compound

HRID 1799280Notes

Reaction equation

HRID 1799280 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+].C(Cl)Cl.[OH:20][C@H:21]([CH3:55])[CH2:22][NH:23][C:24](=[O:54])[CH:25]([NH:38][C:39](=[O:53])[C:40]1[CH:45]=[CH:44][C:43]([O:46][CH2:47][CH2:48][C:49]([F:52])([F:51])[F:50])=[CH:42][CH:41]=1)[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=1>O>[O:54]=[C:24]([NH:23][CH2:22][C:21](=[O:20])[CH3:55])[CH:25]([NH:38][C:39](=[O:53])[C:40]1[CH:45]=[CH:44][C:43]([O:46][CH2:47][CH2:48][C:49]([F:50])([F:51])[F:52])=[CH:42][CH:41]=1)[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 517045Sodium AcetateHCID 57972079HCID 57972079, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 57972109HCID 57972109, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Pyridinium chlorochromate (266 mg, 1.23 mmol) and sodium acetate (20 mg, 0.247 mmol) were added to a methylene chloride (24 mL) solution of N-{2-{[(2R)-2-hydroxypropyl]amino}-2-oxo-1-[4-(trifluoromethoxy)benzyl]ethyl}-4-(3,3,3-trifluoropropoxy)benzamide (322 mg, 0.616 mmol) prepared in Example 74. The mixture was stirred at room temperature for 8 hours, and water (60 mL) was added thereto. The resulting mixture was extracted with methylene chloride (50 mL, three times). The organic layer was dried over anhydrous sodium sulfate, concentrated, and purified by alumina column chromatography (ethyl acetate:methanol, 9:1, V/V) to give 299 mg of the title compound (white powder, yield: 93%).

Workup

  1. extractionThe resulting mixture was extracted with methylene chloride (50 mL, three times)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. custompurified by alumina column chromatography (ethyl acetate:methanol, 9:1, V/V)

Sources & evidence

ORD record
ord-7cfa1d6db24e4e0eaa06930e91f04740
Source dataset
uspto-grants-2013_01
Patent number
US08344029B2

Reaction notes

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