Iodine → 2-Iodo-4-nitro-l-phenylalanine

HRID 429921

Reaktionsgleichung

Reaktionsgleichung von HRID 429921
[I:1]I.[N+:3]([C:6]1[CH:17]=[CH:16][C:9]([CH2:10][C@@H:11]([C:13]([OH:15])=[O:14])[NH2:12])=[CH:8][CH:7]=1)([O-:5])=[O:4].S([O-])([O-])(=O)=S.[Na+].[Na+]>S(=O)(=O)(O)O>[I:1][C:8]1[CH:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:17]=[CH:16][C:9]=1[CH2:10][C@@H:11]([C:13]([OH:15])=[O:14])[NH2:12]

Komponenten

5

Edukt 3

HCID 807IodineHCID 137064-Nitro-3-phenyl-L-alanineHCID 24477Sodium Thiosulfate

Produkt 1

HCID 545742802-Iodo-4-nitro-l-phenylalanine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel2×

Versuchsvorschrift

A 250 mL round bottomed flask equipped with a magnetic stirrer was charged with 60 mL of fuming sulfuric acid (Aldrich) and 12.1 g of iodine (Aldrich). To the resulting dark red solution was added 10.0 g of 4-nitro-L-phenylalanine by slow addition. The flask was fitted with a CaCl2 drying tube and the reaction mixture was. stirred at RT for 18 h. The mixture was then poured onto 300 g of crushed ice. A yellow-brown emulsion resulted which was treated with 7.4 g of sodium thiosulfate and stirred. The resulting light brown suspension was basified to pH=9 by addition of solid NaCO3. This was followed by acidification to pH=5.5 by addition of conc. H2SO4. A brown solid precipitated which was collected by filtration and dried in vacuo. This afforded 6.54 g (41%) of 2-iodo-4-nitro-L-phenylalanine as a brown powder, m.p.>200° C.

Aufarbeitung

  1. customA 250 mL round bottomed flask equipped with a magnetic stirrer
  2. additionby slow addition
  3. customThe flask was fitted with a CaCl2 drying tube
  4. customA yellow-brown emulsion resulted which
  5. stirringstirred
  6. customA brown solid precipitated which
  7. filtrationwas collected by filtration
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6a164d89b53b40be84dd6809e941638f
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06319702B1

Verknüpfte Notizen

Wird geladen…