O-Benzylhydroxylamine → 2-(Benzyloxyaminomethyl)-4-methylpentanoic acid

HRID 982569Notes

Reaction equation

HRID 982569 reaction equation
[CH2:1]([C:5](=[CH2:9])[C:6]([OH:8])=[O:7])[CH:2]([CH3:4])[CH3:3].[CH2:10]([O:17][NH2:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CO>[CH2:10]([O:17][NH:18][CH2:9][CH:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:6]([OH:8])=[O:7])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 102313O-BenzylhydroxylamineHCID 1686594-Methyl-2-methylene valeric acid

Product 1

HCID 193675172-(Benzyloxyaminomethyl)-4-methylpentanoic acidYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.85 g of isobutylacrylic acid and 10.9 g of O-benzylhydroxylamine were heated under reflux in 30 ml of methanol for 8 days. The solvent was removed by evaporation and the residue was dissolved in ethyl acetate and water. The organic layer was washed with 2N hydrochloric acid and water and then extracted six times with 30 ml of 5% sodium hydrogen carbonate solution each time. The aqueous solutions were combined, acidified with 2N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate extract was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated to give an oil which soon crystallized. Trituration with petroleum yielded 1.92 g (35%) of N-benzyloxy 2(RS)-isobutyl-3-aminopropionic acid of melting point 73°-75° C. Rf (toluene/acetic acid 4:1) 0.52.

Workup

  1. customThe solvent was removed by evaporation
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic layer was washed with 2N hydrochloric acid and water
  4. extractionextracted six times with 30 ml of 5% sodium hydrogen carbonate solution each time
  5. extractionextracted with ethyl acetate
  6. extractionThe ethyl acetate extract
  7. washwas washed with water and saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated
  10. customto give an oil which
  11. customsoon crystallized

Sources & evidence

ORD record
ord-e4567fcbdeba44d9af001180a853f253
Source dataset
uspto-grants-1991_02
Patent number
US04996358

Reaction notes

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