Ammonium Acetate → HCID 59331510, compound

HRID 1881956Notes

Reaction equation

HRID 1881956 reaction equation
[CH:1]1([CH2:6][CH:7]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=2)[C:8]([NH:10][CH2:11][C:12](=O)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+:34]>C(O)(=O)C>[CH:1]1([CH2:6][CH:7]([C:8]2[NH:34][C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[CH:11][N:10]=2)[C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 59331516HCID 59331516, compound

Product 1

HCID 59331510HCID 59331510, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution (10 mL) of 3-cyclopentyl-2-[4-(methylsulfonyl)phenyl]-N-(2-oxo-2-pyridin-2-ylethyl)propanamide (330 mg) in acetic acid was added ammonium acetate (310 mg), and the mixture was stirred with heating under reflux for 4 hr. After cooling to room temperature, the reaction mixture was concentrated, the residue was diluted with ethyl acetate, and the mixture was washed with saturated aqueous sodium hydrogen carbonate. The ethyl acetate layer was concentrated, and the residue was subjected to preparative high performance liquid chromatography to give the title compound (80 mg, yield 25%) as colorless amorphous crystals. MS: 396 (MH+).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 4 hr
  3. concentrationthe reaction mixture was concentrated
  4. additionthe residue was diluted with ethyl acetate
  5. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate
  6. concentrationThe ethyl acetate layer was concentrated

Sources & evidence

ORD record
ord-aa97a712cbe64749a959791ee559eafe
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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