Cesium carbonate → HCID 22236096, compound

HRID 1744078Notes

Reaction equation

HRID 1744078 reaction equation
[NH2:1][C:2]1[C:3](=[O:15])[O:4][C:5]([CH3:14])([CH3:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH:17]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:18]([O:20][CH3:21])=[O:19].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[CH3:14][C:5]1([CH3:13])[O:4][C:3](=[O:15])[C:2]([NH:1][CH:17]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:18]([O:20][CH3:21])=[O:19])=[C:6]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 12957039Methyl 2-bromo-4-methylpentanoateHCID 22235995HCID 22235995, compound

Product 1

HCID 22236096HCID 22236096, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 3-amino-5,5-dimethyl-4-phenyl-2(5H)-furanone (175 mg, 0.86 mmol), methyl 2-bromo-4-methylpentanoate (360 mg, 1.73 mmol) and cesium carbonate (310 mg, 0.95 mmol) in DMF (4 mL) was heated to 130° C. for 18 h. The mixture was cooled, diluted with EtOAc and washed with water (2×) and brine, then dried over MgSO4 and concentrated. Purification by flash chromatography (20% EtOAc/hexanes) provided methyl 2-[(5,5-dimethyl-2-oxo-4-phenyl-2,5-dihydro-3-furanyl)amino]-4-methylpentanoate.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with water (2×) and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customPurification by flash chromatography (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d0ef81caf267474e88d0bf6692d06940
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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