Water → HCID 178502650, compound

HRID 1504289Notes

Reaction equation

HRID 1504289 reaction equation
[OH:1][C:2]1[N:6]([C:7]([CH3:16])([CH3:15])[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([CH:17]([CH3:19])[CH3:18])[C:3]=1[C:20](=O)[CH3:21].Cl.[CH3:24][O:25][NH2:26].C([O-])(=O)C.[Na+].O>C(O)C>[CH3:24][O:25][N:26]=[C:20]([C:3]1[C:4]([CH:17]([CH3:19])[CH3:18])=[N:5][N:6]([C:7]([CH3:16])([CH3:15])[CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:2]=1[OH:1])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 178466617HCID 178466617, compound

Product 1

HCID 178502650HCID 178502650, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

150 mg (0.50 mmol) of 1-(5-hydroxy-3-isopropyl-1-(2-methyl-1-phenylpropan-2-yl)-1H-pyrazol-4-yl)ethanone, 209 mg (2.50 mmol) of methoxyamine hydrochloride and 286 mg (3.49 mmol) of sodium acetate were mixed with 1.3 ml of distilled water and 1.3 ml of ethanol and stirred at room temperature for 16 hours. After completion of the reaction, the reaction solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (silica gel 4 g, ethyl acetate:hexane=1:99) to give 70 mg of the desired product as an orange oil.

Workup

  1. customAfter completion of the reaction
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (silica gel 4 g, ethyl acetate:hexane=1:99)

Sources & evidence

ORD record
ord-2ed4f7bac18246a8a71b759dfa08e5d0
Source dataset
uspto-grants-2015_12
Patent number
US09212348B2

Reaction notes

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