Sodium Hydroxide → L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-

HRID 434483Notes

Reaction equation

HRID 434483 reaction equation
[C:1]([NH:8][C@H:9]([CH2:14][OH:15])[CH2:10][CH:11]([CH3:13])[CH3:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[Na+].[O-:18][Mn](=O)(=O)=O.[K+]>CO>[C:1]([NH:8][C@H:9]([C:14]([OH:18])=[O:15])[CH2:10][CH:11]([CH3:12])[CH3:13])([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 7018766Boc-L-leucinol

Product 1

HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-Yield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

BOC-leucinol (130 mg, 0.598 mmol) was treated with 3.1 ml of 0.25 N NaOH followed by KMnO4 (125 mg, 0.796 mmol) at room temperature and stirred 15 min. The reaction was treated with methanol, stirred 15 min, and the brown precipitate removed by filtration through Celite. The filtrate was acidified with solid citric acid and extracted with ether (3×). The combined ethereal extracts were washed with saturated NaCl (aq) (2×), dried over MgSO4 and filtered. Evaporation of the filtrate in vacuo gave 130 mg of BOC-leucine as an oil homogeneous by TLC (Rf, 0.34; silica GF in 5% MeOH/95% CH2Cl2).

Workup

  1. stirringstirred 15 min
  2. customthe brown precipitate removed by filtration through Celite
  3. extractionextracted with ether (3×)
  4. washThe combined ethereal extracts were washed with saturated NaCl (aq) (2×)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customEvaporation of the filtrate in vacuo

Sources & evidence

ORD record
ord-85a54eb6d99d427eb2445ca1cf30736e
Source dataset
uspto-grants-1983_08
Patent number
US04397786

Reaction notes

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