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

HRID 434483Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 434483
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-85a54eb6d99d427eb2445ca1cf30736e
Quelldatensatz
uspto-grants-1983_08
Patentnummer
US04397786

Notizen zur Reaktion

Wird geladen…