L-Leucine → N-(3,5-dinitrobenzoyl)leucine

HRID 21349

Reaktionsgleichung

Reaktionsgleichung von HRID 21349
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[N+:10]([C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([N+:22]([O-:24])=[O:23])[CH:21]=1)[C:16](Cl)=[O:17])([O-:12])=[O:11].C1OC1C>O1CCCC1>[N+:10]([C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([N+:22]([O-:24])=[O:23])[CH:21]=1)[C:16]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])=[O:17])([O-:12])=[O:11]

Komponenten

5

Edukt 3

HCID 6106L-LeucineHCID 6378Propylene OxideHCID 74323,5-Dinitrobenzoyl chloride2×

Produkt 1

HCID 101111N-(3,5-dinitrobenzoyl)leucine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(S)-Leucine (10 g) was suspended in 150 mL dry tetrahydrofuran and chilled in an ice bath while stirring under a nitrogen atmosphere. 3,5-Dinitrobenzoyl chloride (Table 2, Compound 13, 21 g) and propylene oxide (6.6 g) were added; the resulting heterogeneous mixture became clear after several minutes. The mixture was allowed to stir for 5 h, and was evaporated under reduced pressure to afford an oil which crystallized upon addition of 100 mL of cold dichloromethane. Filtration and drying of the resulting crystals afforded 3,5-dinitrobenzoyl-(S)-leucine, 14, as a white solid (20.64 g, 83% yield). 1H NMR (200 MHz, d6DMSO) δ: 0.95 (m,6H), 1.75 (M,3H), 4.25 (m,1H), 9.00 (t,1H), 9.17 (d,2H), 9.41 (d,1H).

Aufarbeitung

  1. temperaturechilled in an ice bath
  2. waitthe resulting heterogeneous mixture became clear after several minutes
  3. stirringto stir for 5 h
  4. customwas evaporated under reduced pressure
  5. customto afford an oil which
  6. customcrystallized upon addition of 100 mL of cold dichloromethane
  7. filtrationFiltration
  8. customdrying of the resulting crystals

Quellen und Nachweise

ORD-Eintrag
ord-cff01e4621d34ba1acb7697f62712f46
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05422004

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