Ammonium Acetate → HCID 59331420, compound

HRID 1881951Notes

Reaction equation

HRID 1881951 reaction equation
[CH:1]1([CH2:6][CH:7]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)[C:8](=O)[CH2:9][CH2:10][C:11]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+:33]>CN(C)C=O.C(OCC)(=O)C>[CH:1]1([CH2:6][CH:7]([C:8]2[NH:33][C:11]([C:13]3[S:14][CH:15]=[CH:16][N:17]=3)=[CH:10][CH:9]=2)[C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 517165Ammonium AcetateHCID 59331244HCID 59331244, compound

Product 1

HCID 59331420HCID 59331420, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution (5 mL) of 6-cyclopentyl-5-[4-(methylsulfonyl)phenyl]-1-(1,3-thiazol-2-yl)hexane-1,4-dione (300 mg) in N,N-dimethylformamide was added ammonium acetate (310 mg), and the mixture was stirred at 100° C. for 1.5 hr. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (150 mg, yield 53%) was obtained as colorless amorphous crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS: 401 (MH+).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-59999f78613447a1b05bbf324f4f63ec
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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