Sodium Hydroxide → HCID 58192797, compound

HRID 2361717Notes

Reaction equation

HRID 2361717 reaction equation
O=[C:2]1[CH:9]2[CH2:10][C:5]3([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.[NH2:20][OH:21].Cl.[OH-].[Na+]>CCO.O>[OH:21][N:20]=[C:2]1[CH:9]2[CH2:10][C:5]3([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 58192767HCID 58192767, compound

Product 1

HCID 58192797HCID 58192797, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of ketone 1C (3 0 mmol), NH2OH—HCl (5 mmol), and NaOH (5 mmol) was diluted with EtOH (5 mL) and H2O (1 mL) and the reaction mixture was heated at 80° C. for 16 h. Upon cooling, the reaction mixture was extracted with DCM (10 mL×3) and the combined organic layers were dried (Na2SO4) and concentrated to provide oxime 14A in 90% yield as a solid. The material was used in the next step without further purification. Data: LC/MS (ESR) m/z 281 [M+1]+.

Workup

  1. temperatureUpon cooling
  2. extractionthe reaction mixture was extracted with DCM (10 mL×3)
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-778f2c2a02be4a0e969c79e794149b52
Source dataset
uspto-grants-2014_04
Patent number
US08691808B2

Reaction notes

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