Potassium Hydroxide → HCID 21866788, compound

HRID 857253Notes

Reaction equation

HRID 857253 reaction equation
[CH3:1][C:2]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[N:17]=[C:18]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[O:19][C:20]=1[CH3:21])([CH3:8])[C:3](OCC)=[O:4].[Cl-].[OH:30][NH3+:31].[OH-].[K+]>CO>[CH3:1][C:2]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[N:17]=[C:18]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[O:19][C:20]=1[CH3:21])([CH3:8])[C:3]([NH:31][OH:30])=[O:4]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 21645Hydroxylamine HClHCID 21866780HCID 21866780, compound

Product 1

HCID 21866788HCID 21866788, compoundYield 104.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 20 ml of a solution of 4.84 g of ethyl 2-methyl-2-{6-[5-methyl-2-(p-tolyl)oxazol-4-yl]hexyloxy}propionate in methanol, 3.47 g of hydroxylammonium chloride was added, and then 12.5 ml of solution of 5 M potassium hydroxide in methanol was added dropwise slowly under ice-cooling with stirring. The ice-bath was removed and the mixture was stirred for 36 hours at room temperature. The reaction solution was concentrated. The residue was acidified with 50% aqueous acetic acid solution, water was added thereto and extracted with ethyl acetate. The organic layer was washed with water and brine serially, dried over anhydrous magnesium sulfate and concentrated. The residue was concentrated after addition of toluene, and again concentrated after addition of ethanol to provide 4.90 g of the objective compound as pale yellow oil.

Workup

  1. temperaturecooling
  2. customThe ice-bath was removed
  3. stirringthe mixture was stirred for 36 hours at room temperature
  4. concentrationThe reaction solution was concentrated
  5. additionwas added
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water and brine serially
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. concentrationThe residue was concentrated
  11. additionafter addition of toluene
  12. concentrationagain concentrated
  13. additionafter addition of ethanol

Sources & evidence

ORD record
ord-fd0eefb70c7f441baaa35c678670dd3f
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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